visit winter park fl

Things to do in Winter Park to experience its special charm

By: Author Bonnie Gross

Posted on Last updated: August 5, 2024

For 140 years visitors have come to explore the many charms of Winter Park, a tree-filled small city now engulfed by metropolitan Orlando. Originally, they came by train.

I decided Winter Park was the perfect modern-day destination to reach by train, combining a “romantic rail journey” with a walkable town. I was right – except for the “romantic rail journey” part. But more on that later.

While Amtrak left a lot to be desired, Winter Park lived up to expectations. In a three-night stay, we walked everywhere. There were enough things to do in Winter Park that I left wishing I had time to get to one additional museum and one more great park.

Winter Park started as a resort for rich northerners fleeing cold weather in the 1800s. With its chain of six sparkling lakes, it soon became a place where wealthy folks built grand winter homes.

Winter Park Sidewalk Art Festival , Winter Park, March 15-17, 2024. This large show annually earns top ranking among art festivals nationwide. In addition to the draw of high-quality art, it offers activities to entertain various ages and interests. Be aware: It draws a big crowd.

Winter Park has remained decidedly upscale and has benefited from all the resources associated with wealth over the years.

Its rich residents developed a few museums that are real gems, a fabulous nearby botanical garden and Rollins College, a private college with a beautiful campus.

There is even a touristy but fun Scenic Boat Tour, operating since 1938.

It’s all compact and walkable (our grand tour required only one $10 Uber ride). Winter Park still has many red-brick streets and historic homes and buildings. In short, I found lots of things to do in Winter Park to make a great Florida getaway.

We arrived at the very cute retro-looking train depot, also a busy stop for the regional SunRail system. When you reach the town this way, everything that surrounds you is full of Winter Park history and charm.

The center of the city has an attractive Central Park with an arbor of gorgeous purple wisteria blooming profusely in March. There are fountains and benches and open space for families and sweethearts to enjoy.

Paralleling the train tracks is Park Avenue, lined with a wide variety of great restaurants, coffee shops, wine bars, a chocolatier, a fabulous French bakery and trendy shops.

On one end of the shopping district is the Charles Hosmer Morse Museum of American Art, very much worth visiting.

At the other, Park Avenue leads to the lovely campus of Rollins Campus, where you can take a scenic walk along Lake Virginia and visit the free art museum.

Park Avenue has big shady trees and planters bursting with colorful flowers.

Off Park Avenue, you can walk a few blocks on New England Avenue across the tracks to the lively Hannibal Square district , also full of restaurants and cafes along the red-brick road.

On the way, at the side of the train tracks is the small but impressive Winter Park History Museum.

Planning your visit to Winter Park

It’s not every Florida town where you can plan two days of activities on foot, but the heart of Winter Park is compact, developed before cars dominated the city.

We arrived on a Sunday night, which meant our first day in town was a Monday —  actually not a great idea. All the museums are closed on Monday, as well as several restaurants. But our first day was packed full of fun including two botanical gardens and the Scenic Boat Tour.

Enjoying Margarita Mondays ($5 and terrific) at Pepe’s Cantina in the Hannibal Square neighborhood made it all worthwhile. Day two, then, was dominated by museums.

Eight great things to do in Winter Park

1. The Charles Hosmer Morse Museum of American Art

This is the top attraction in Winter Park. The Morse Museum is known for its collection of works by Louis Comfort Tiffany and, as a result, it has eye candy that will appeal to even people who don’t normally like art museums.

The examples of Tiffany glass here are luminous, colorful and easy to appreciate. You can breeze through in 45 minutes or, if you get captivated by Tiffany and his life, you could easily spend two hours.

We particularly enjoyed the several galleries devoted to Tiffany’s Long Island mansion, Laurelton Hall, which burned down. His home there, where his work went far beyond windows and lamps, was one of his masterpieces.

The founders of the Morse Museum, Hugh McKean and Jeannette Genius McKean, had the items that would be salvaged brought to the museum where they are now displayed. This includes parts of several rooms, such as an entire arbor with magnificent daffodil ornamental columns.

The museum is closed on Mondays.

Admission is inexpensive , so you have no excuse to miss it. It’s $6 adults; $5 seniors; $1 students (with valid ID) and free for children younger than 12. In addition it is free to all Fridays from 4 p.m. to 8 p.m.!

Charles Hosmer Morse Museum of American Art 445 N. Park Ave., Winter Park, FL 32789 (407) 645-5311

2. Winter Park Scenic Boat Tour

Visitors to Winter Park have been delighting in this boat tour since 1938. The boats only hold 18 people and they do not have canopies because the narrow canals that connect the Winter Park chain of lakes go under bridges that are only inches above your head.

This is your classic Florida tourist experience, complete with the corny guide telling the same groan-worthy jokes on every cruise. But it has been around for more than 80 years for a reason – spectacular scenery you’ll only see this way.  

Who among us does not want to gaze at magnificent mansions with boat houses prettier than our own home?

The highlight, though, is threading through Winter Park’s very narrow canals connecting the lakes, where trees hang overhead and flowers bloom in lushly landscaped yards.

The tour provides interesting history of Winter Park and shows you several notable buildings and the Rollins College campus from the water. We also liked that on this boat tour, the driver hits the gas pedal occasionally, providing a whoosh of speed and a breeze.

The tours are exactly an hour long, which is perfect, and are offered hourly with no reservations (except for large groups). It’s an inexpensive thing to add to your day – tickets are $16 adults; $8 ages 2 to 11.

Winter Park Scenic Boat Tours 312 E. Morse Blvd. Winter Park, FL 32789 407-644-4056.

3. Albin Polasek Museum and Sculpture Garden

I have to admit, I had never heard of Albin Polasek, but the sculptor’s 1949 home and gardens on Lake Osceola is a real hidden gem and worth a stop.

Polasek was a successful and well known 20th Century sculptor who led the Chicago Art Institute’s sculpture program for many years. Born in what is now the Czech Republic, Polasek retired to Winter Park and built a lake home and studio with a magnificent view.

Visitors get a brief tour of the home — it is not huge but the interior is filled with his art and it’s quite interesting to see. The gardens display dozens of sculptures, surrounded by Florida plants, flowers and trees along the shore of Lake Osceola.

Many of the works have a religious character, but many others are nudes. Some have a personal touch, such as the painting where he inserted his face into the Stations of the Cross among the holy people at the foot of the crucifixion.

The museum and grounds can be seen in an hour or two, but you also can linger at the picnic tables in the garden. The museum is closed on Mondays. Admission is $12 for adults.

Albin Polasek Museum and Sculpture Garden 633 Osceola Ave., Winter Park, FL 32789 (407) 647-6294

4. Things to do in Winter Park: Strolling the grounds of Rollins College and visiting its free art museum

In 2015, the campus of Rollins College was named the most beautiful in the nation by the Princeton Review and it makes for a beautiful walk.

You can reach the campus in 10 minutes from downtown. Just go to the southern end of South Park Avenue and cross busy Fairbanks Avenue.

The campus has many handsome historic buildings in the Mediterranean revival style framed by sprawling live oaks and overlooking Lake Virginia.

There is a half mile lakeshore walk through the campus, along which is the free Rollins College Museum of Art. It’s a small museum that gets high marks for its quality, displaying visiting exhibits as well as items from its own collection. (Just like the other two art museums in town, it’s closed on Mondays.)

At the northern end of the campus is a city park called Dinky Dock Park, where you’ll find locals fishing and launching kayaks into Lake Virginia. There is free parking here, but spaces aren’t always easy to get.

Rollins College Museum of Art 1000 Holt Ave., Winter Park, FL 32789 (407) 646-2000

5. Mead Botanical Garden

This free garden is a half hour walk from the heart of downtown. We enjoyed walking along red brick roads through historic neighborhoods to reach it.

Mead Botanical Garden has some beautifully landscaped spaces with colorful planters as well as camellias and azaleas, which were in bloom for our March visit.

The 47-acre garden has plenty of wilder terrain too, and offers hiking trails, picturesque bridges, a pond and a creek. I particularly liked the small creek lined with cypress knees. There are mansions across the water.

Mead Botanical Garden 1300 S Denning Drive, Winter Park, FL 32789 (407) 622-6323

6. Harry P. Leu Botanical Gardens

While technically not in Winter Park, Leu Botanical Garden is so close to Winter Park that we walked there from Mead Botanical Garden. Most people would drive or Uber, I suspect; it’s a long but scenic walk. By the time we’d explored the garden, we were foot-sore and took an Uber back to our hotel for a reasonable $10. It’s a 3-mile walk.

This 50-acre botanical garden could be the most beautiful place in Orlando.

With towering mature trees giving shade and Lake Rowena providing a beautiful backdrop, the gardens unveil beauty at every turn – and there are many turns in the winding walkways.

You’ll find different favorites at different times of year. There is a big rose garden, which was not flowering much on our visit, but we enjoyed the camellias in its extensive collection.

A favorite year ‘round is the tropical stream, lush with fascinating specimens, all of which are carefully labeled.

The garden has an Old Florida feel and contains the Leu House Museum, a restored 19th Century home listed on the National Register of Historic Places that has been owned by only four families.

Birds and wildlife abound. On one visit, we saw otters in Lake Rowena.

Admission is $15 adults; $10 for children 4 to 17.

Harry P. Leu Botanical Gardens 1920 N. Forest Ave., Orlando, FL 32803 (407) 246-2620

7. Take a walk to Kraft Azalea Park

A mile north of the Morse Museum and downtown Winter Park is another special park. It’s a half hour walk through some of the beautiful residential streets of Winter Park.

A few highlights of the walk: Be sure to stop to gaze at Casa Feliz Historic Home at 656 Park Ave. This special-event venue is not currently open for tours, but the 1932 “Andalusian farmhouse” is a beauty to admire from outside.

Plan your route so you cross the Venetian Canal at Alabama Drive and Palmer Avenue. This is one of the picturesque canals the Scenic Boat Tour takes visitors through.

You can stop and grab a bench at Kraft Azalea Park. It’s only five acres, but this free public garden packs in a lot of beauty. The park occupies a peninsula in Lake Maitland and is full of gorgeous shading trees hanging with Spanish moss. It includes one of the largest banyan trees you’ll find this far north.

It is also home to a great egret rookery. ( Details are here .) Every year between February and early June, about 50 nesting pairs take up residence here.

The park has benches, a dock and its Exedra Monument, in the style of ancient Greece, is popular for weddings.

Kraft Azalea Gardens 1365 Alabama Drive, Winter Park, FL 32789 (407) 599-3334

8. Things to do in Winter Park: Dine, drink, sample wine, chocolates, coffee, pastries and more

The downtown Winter Park area is full of culinary treats.

There are adorable coffee shops — CFS Coffee in Hannibal Square smelled divine with cute outdoor seating and folks rave about New General just off Park Avenue.

For wine bars, you’ll pass two highly rated ones on Park Avenue — The Wine Room on Park Avenue and the Parkview.

The chocolates and cookies were so tempting in Peterbrooke Chocolatier on Park Avenue and Croissant Gourmet , just off Park Avenue at 120 E. Morse Blvd., is full of treats, as well as being a good place to buy a sandwich for the train.

And the restaurants? You’ll find every kind of place to dine, many within walking distance. Consult Yelp and TripAdvisor for tips.

Here are three perennial favorites on Park Avenue:

Prato , 124 N Park Ave., Winter Park, 32789. It’s the downtown spot for all things Italian, from pizza to meatballs to the salads and soups. It also gets high marks for its view of Park Avenue and the ambiance.

The Parkview , 136 S Park Ave., Winter Park, 32789. While primarily a wine and beer bar, the dinner menu has a nice selection of sandwiches, salads, flatbreads and a few special entrees.

Boca , 358 N Park Ave, Winter Park. This is a hopping spot that can get loud. It offers an eclectic menu and is popular for lunch.

Hotels in Winter Park FL: Two good choices downtown

We stayed in the historic Park Plaza Hotel , which has a perfect location in the center of downtown, a block from the train station overlooking both Central Park and Park Avenue.

We love historic hotels, and flaws that others note  – tiny bathrooms, small rooms – are fine by us. They come with staying in what I consider a charming one-of-a-kind hotel with character. This one turned 100 in 2022!

Two things I particularly loved about the Park Plaza Hotel: its ancient elevator with the metal grate you manually close before the elevator moves and the tasty continental breakfast brought to the room on a wooden tray when you call the front desk.

The fresh croissant and container of coffee were ideal, though the rooms are so small there was barely a place to sit and enjoy it.

Next time I’ll try to book the more expensive balcony rooms, which have plant-filled balconies where such a breakfast could be best enjoyed. As it is, during high season in March 2022, our room was $159 thanks to the “Florida resident” rate – reasonable for its outstanding location.

There is another downtown hotel that is newer, fancier and a bit more expensive – the Alphond Inn , operated by Rollins College. Profits help support the college and it offers some great sounding packages. The Alphond is four blocks from the train station, so it also has an excellent location.

Park Plaza Hotel 307 S. Park Ave., Winter Park, FL 32789  (407) 647-1072

Alphond Inn 300 E. New England Ave., Winter Park, FL 32789 (407) 998-8090

Hotels in Winter Park on Hotels.com

Vacation rentals in Winter Park on VRBO

Taking Amtrak to Winter Park

I had long wanted to take Amtrak on a Florida Rambler trip, and I knew Winter Park was ideal because of its charming downtown built around the railroad station.

So when I heard that Amtrak was having a BOGO sale, which was about to end, I quickly booked a round-trip ticket for my husband and me. What a deal! Only $48 roundtrip from our Fort Lauderdale home for both of us!

The problem is: I didn’t look at the route or the length of the journey. It was only when we were waiting ….and waiting….and waiting for the train to arrive in Fort Lauderdale – only its third stop from its starting location! – that I learned that the train goes to Winter Park via Tampa. And it was more than a seven hour trip, IF it was on time, which it was not, and maybe never is.

The only train available is a daily trip on the Silver Star. A shorter route, skipping the side trip to Tampa, is offered on the Silver Meteor, which is currently out of service, returning perhaps at some point in 2022.

As it turns out, our journey started 90 minutes late and we lost time as we travelled. The Silver Star’s route goes through Lakeland twice, as it veers off to Tampa and back.

The seating is large and feels luxurious compared to airplane travel, and we enjoyed looking out the windows. But the food was abysmal. (A variety of plastic wrapped sandwiches heated in a microwave.)

On our return from Winter Park, the train was not very clean, which is not surprising since it was on its last few hours of a 1,522-mile route between New York City and Miami via Washington, D.C. At least one of the bathrooms was unusable as a result.

I have to admit: I’ll do better research if I ever do it again. I do love train travel, though, and I believe in finding alternatives to cars.

So I think it might work from Tampa or Jacksonville as a way to visit Winter Park. Also: Within the greater Orlando area, you could use the SunRail system to have a weekend getaway by rail in Winter Park.

From the minute I stepped off the train to the moment I boarded for our return, I loved Winter Park. But in this case, getting there was not half the fun.

More things to do in Orlando area

• Eight natural places to enjoy in Orlando area
• Moss Park offers great camping near Disney
• Winter Garden: Old Florida town thrives around great bike trail
• West Orange Trail: Impressive bike trail in Central Florida
• Van Fleet Trail: 29 miles of beauty by bike near Orlando
• Wekiva River Basin’s stunning beauty invites paddlers, campers, hikers and bikers

The author, Bonnie Gross, travels with her husband David Blasco, discovering off-the-beaten path places to hike, kayak, bike, swim and explore. Florida Rambler was founded in 2010 by Bonnie and fellow journalist Bob Rountree, two long-time Florida residents who have spent decades exploring the Florida outdoors. Their articles have been published in the Sun Sentinel, the Miami Herald, the Orlando Sentinel, The Guardian and Visit Florida.

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Dave Cannon

Tuesday 15th of March 2022

Bonnie, nice article about my town, but you write, " spectacular scenery you’ll only see this way." in the Scenic Boat Tour section. If I had not been reading Florida Rambler for the last 10 plus years, I would think you had never been in a kayak. Also, there are six lakes in the Winter Park Chain. Lakes Minnehaha and Nina are in Maitland, Lake Maitland is half in Maitland and half in Winter Park. Did your tour boat captain tell you to spit on the Maitland side? Lakes Osceola, Virgina, and Mizel are in Winter Park. Maps do show Lake Berry, but it is not connected.

Bonnie Gross

Thanks Dave. Great town. You made me laugh. I DID think about that phrase "scenery you'll only see this way" in regards to kayaks. I love kayaking, of course. But these are bigger lakes and you'd be paddling long and hard to cover the equivalent scenery of multiple lakes and canals. (Plus, I find lake kayaking a little boring. You paddle and paddle and the scenery changes so slowly.) Also: I AM a little confused about all the lakes. I've seen references to seven lakes in the chain; others say six lakes, and some places say five! I guess it depends what/how you count? I appreciate you reading Rambler all these years, Dave!

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• Destinations

This Charming Florida City Near Orlando Is the Perfect Break From the Theme Park Crowds

Even though Winter Park is near Orlando's theme parks, it feels leaps and bounds away.

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Cobblestone streets dotted with Michelin-recognized restaurants and locally owned shops, lakes with boat tours, and grassy areas for kids to play tag and fly kites: This is Winter Park, Florida. A hop, skip, and a jump from Orlando’s theme park scene, this town chartered in 1887 thrills in other ways. Its original purpose still holds true: New Englanders founded it as an escape from cold weather. But since that time, the 10-square-mile city has become a year-round destination. Orlando residents love the place, but they can’t keep it a secret anymore. No matter why you’re in the Orlando area, a few days in Winter Park would provide a welcome respite before heading home. In fact, the town has so much going for it, we’d argue that it merits a trip on its own.

Downtown, Park Avenue — where stand-out restaurants and local boutiques dot the brick streets — is the place to be. Just off Park Avenue, Rollins, a small liberal arts college founded 135 years ago, contributes to the town’s robust array of cultural activities. A short walk from downtown lies the waterfront, where six lakes are connected by navigable canals. Ready to plan a trip to this charming city? Here's what you need to know.

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Best Things to Do in Winter Park

If you like culture, nature, and shopping, Winter Park will be a new favorite. With a rose garden and beautiful fountains, 11-acre Central Park on Park Avenue hosts many of the city’s festivals and events, including holiday festivities and the Olde Fashioned Fourth of July Celebration. It’s also the perfect place to take the kids to burn off steam in between visiting stores or before going back to the hotel.

More spectacular than you’d imagine, the Morse Museum , located on Park Avenue, features a large collection of Tiffany works as well as other American art. The stunning chapel, which was crafted for the Chicago World’s Fair, is a must-see.

When you’re ready for a break from walking, take the hour-long Scenic Boat Tour around Winter Park’s many lakes, where you'll spot beautiful homes while you learn more about the city's history. Kids of all ages are welcome (even encouraged) to join the fun on the 18-passenger pontoon boats. Water sports, like paddleboarding and kayaking, are also popular around the lakes.

On Saturday mornings, dozens of vendors sell their produce, bread, sweets, and more at the Saturday Farmers’ Market . It's the perfect place to grab ingredients before heading to a park for a picnic lunch.

Save room in your suitcase to treat yourself to an item from one of the many one-of-a-kind shops in Winter Park. You’ll swoon over the stationary and artsy decorative items at Rifle Paper Co. ’s own store (the brand is based in Winter Park).

Local teens and college students shop at Avalon Exchange , a thrift shop that’s clean, organized, and budget friendly with a mix of retro and popular brands. Stop by Loving Thyself Rocks if for nothing else than to get a selfie sitting on the winged crystal chair at the entrance. Writer’s Block bookstore offers a well-curated selection for kids and adults (plus a fantastic name).

Winter Park Hotels

While visitors only have a handful of lodging options in Winter Park, the surrounding area opens up a multitude of possibilities.

Established more than 130 years ago, The Alfond Inn at Rollins is getting better with age. Sprinkled with incredible paintings from the Rollins Art Museum, the recently renovated lobby is a design masterpiece and fosters family togetherness thanks to a variety of seating arrangements and a corner chess set. An expansion, which will add a new spa and a wing to the inn’s current 112 guest rooms, is expected to wrap up by the end of the year. The location, just a few blocks from Park Avenue, is stellar.

With 28 guest rooms — some with original brick walls — the Park Plaza Hotel is the only place to stay on the city’s famed Park Avenue. There are balcony rooms and suites for people-watching.

About eight miles from Winter Park, Sonder Wellborn is located in the oldest house in the Orlando area. Suites are well priced and spacious, plus the property includes a Victorian garden.

If you’re combining a business trip to the Orlando Convention Center with a visit to Winter Park, the AC Hotel Marriott Downtown Orlando is a great choice. The eight-floor, 180-room property boasts a SkyBar Rooftop Terrace with incredible city views. It’s just eight miles from Winter Park.

Visit Florida

Best Time to Visit Winter Park

While you’ll have fun no matter when you go to Winter Park, shifts in weather and special programming favor certain months.

Despite its name, the most comfortable season to visit Winter Park is spring — and the earlier, the better. March feels glorious with average high temperatures reaching about 76 degrees Fahrenheit and the lowest humidity of the year. It’s no coincidence that the organizers of the city’s annual Sidewalk Art Festival, which attracts 350,000 visitors, schedule it for March. It’s a little cooler in February and warmer in April, but still pleasant. You won’t find many April showers in Winter Park — April is the second-least rainy month.

The holidays usher in another magical time to explore Winter Park, especially if you’re bringing children. Two big events take place during the first weekend of December. On Friday, “Winter on the Avenue” transforms Central Park into a holiday wonderland, complete with snow slides, s’mores, and strolling carolers. Everyone gathers around for the lighting of the Christmas tree and menorah. The next day, music fills the streets for the Ye Olde Hometown Christmas Parade. A tradition for more than 70 years, the parade’s headliners include marching bands, fire trucks, and Santa Claus. Winter Park’s weather by far outshines the North Pole, with average December highs in the mid-70s.

Families who have to plan their vacations around school calendars and practice schedules may not be able to avoid a summertime visit. Although it’s typically hot, humid, and rainy, scheduling outdoor activities for the morning or evening will make it less likely that Florida’s temperamental summer weather will interfere with your fun.

Where to Eat and Drink

Orlando locals flock to Winter Park for memorable meals — whether they’re bringing the entire family or looking for a romantic table for two. Winter Park serves up a variety of cuisines and vibes at its top food establishments.

At Briarpatch , the most iconic eatery on Park Avenue, locals line up for mimosas and delicious brunch offerings (think: brown butter Belgian waffles and raspberry lemon cream pancakes.) The housemade cakes — carrot, chocolate layer, and red velvet — are as Instagrammable as they are tasty. You can dine al fresco on the outdoor tables overlooking Central Park or opt for the indoor seating; the dining room oozes Southern charm.

Fresh from earning a Michelin star, Soseki , a 10-seat Japanese restaurant, specializes in a divine multi-course dining experience based on the best ingredients that its farmers, fishermen, and cheese purveyors offer.

With husband-and-wife, James Beard-nominated chefs in the kitchen, The Ravenous Pig hits the spot with a variety of apps, hand-helds, innovative cocktails, and other gastropub fare.

If the kids want pizza, Prato is the place for your family. Request a table on the patio (isn’t there something about eating outside that makes kids less wiggly?) and order them a margarita pie to share while you pick one of the other modern Italian dishes made with locally sourced ingredients.

Getting There

Winter Park is easily accessible by car and airplane. You probably won’t use your car much once you’re in town.

If you’re coming from one of Orlando’s theme parks, the ride will be relatively short. Winter Park is about 30 miles north of Disney’s Magic Kingdom and 15 miles north of Universal Florida on I-4. Tampa, Jacksonville, and Melbourne, Florida are all within two hours or so.

The closest airport is Orlando International Airport, which is about a 30-minute drive to Winter Park. Later in 2023, the Brightline Train’ s airport station will connect the city with Miami, Boca Raton, West Palm Beach, and Fort Lauderdale. If you can fly into the smaller (and far less crowded) Orlando Sanford International Airport, you’d still only have about a half-hour drive.

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Winter Park FAQs

What is Winter Park known for?

The City of Winter Park is one of Central Florida’s most visited communities in large part to the award-winning restaurants, sidewalk shopping, acclaimed arts and more in the upscale Park Avenue District. The city also has much for outdoor enthusiasts, including a robust parks system and the gorgeous Winter Park Chain of Lakes.

How far is Winter Park from Walt Disney World® Resort?

Winter Park is about 35 minutes northeast of Walt Disney World.

How far is Winter Park from the beach?

Florida’s east coast beaches are an hour or less from Winter Park. West coast beaches are approximately two hours away.

How far is Winter Park from downtown Orlando?

Winter Park is approximately 20 minutes northeast of downtown Orlando.

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Home » Destinations » Winter Park

Winter Park

• Visitor Center: 151 W. Lyman Ave., Winter Park, FL 32789
• Phone: 407) 644-8281
• Email: [email protected]

Destination Highlights

Things to do in winter park.

Just 30 minutes north of Orlando, a visit to Winter Park is the perfect addition to a central Florida vacation. This small city is home to world-class museums, upscale boutiques and shopping, fine-dining restaurants, sidewalk cafes, and luxury accommodations, all with the feel of a European village - it’s a world away from the crowded theme parks. Discover more about beautiful Winter Park.

Did You Know?

Interesting & useful facts

Originally a winter resort town, Winter Park is now known for its leafy green spaces, lakes, museums & boutiques

The Winter Park Chain of Lakes is a series of lakes linked by a network of canals.

Boat rides, kayaking & paddle-boarding are popular activities on the Winter Park Chain of Lakes

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Indulge – Park Avenue

Winter Park’s shopping, dining and cultural gem boasts more than 140 boutiques, sidewalk cafes and fine-dining restaurants, and museums, all in the shadow of oak-canopied central park. Historic Park Avenue lures you in while richly treating your senses. The aromas of dishes from around the world – Italy, Turkey, France – draw you to bistros and wine bars for experiences you won’t forget.

Downtown Winter Park’s charm is magnified in the truly unique details: hidden gardens and side streets that are home to locally-owned shops, a farmer’s market that attracts both local and visitors alike each Saturday morning, festive parades that mark the seasons and a scenic boat tour that cruises the canals between the City’s lakes overlooking the area’s most prestigious homes.

Conveniently located on Park Avenue in the heart of downtown is an 11-acre park that boasts shady oak trees, landscaped planters, sitting areas, open space and three beautiful fountains. The park welcomes visitors to the city that arrive by train and hosts numerous events throughout the year, including the Winter Park Sidewalk Art Festival, Winter Park Autumn Art Festival, and the Olde Fashioned 4th of July Celebration.

The anchor of Park Avenue, the Winter Park Golf Course, is the second oldest golf club in the Central Florida area. The golf course opened in 1914 and, after its recent renovation, was named a top 10 short course in the USA by Golf Advisor. The course makes its way through the downtown Winter Park area and provides a challenge to even the most experienced golfer. With its narrow, tree-lined fairways and postage stamp, bunker guarded greens, this course will provide a test for every shot in a golfer’s arsenal. Daily fees start at $14 to walk 9 holes for non-residents.

Illuminate – Alfond Inn & Rollins College

Located along the banks of Lake Virginia at the south tip of Park Avenue, the beautiful Rollins College campus encourages visitors to take advantage of Florida’s natural beauty and Winter Park’s history and charm. With its Spanish-Mediterranean architecture, lush grounds and gorgeous setting, Rollins was named one of the 25 Most Beautiful College Campuses in 2017 by Condé Nast.

Be sure to visit the college’s award-winning boutique hotel, the Alfond Inn. Art provides the canvas at the Alfond Inn, designed as the imaginative extension of the Cornell Fine Arts Museum. Eye-opening and provocative, the art is integral, whether you’re staying in the Inn’s luxury suites, dining at Hamilton’s Kitchen or sipping cocktails in the captivating lounge, just a stone’s throw away from Park Avenue.

Inspire – Arts & Culture

Enter a world of infinite arts and culture spaces in Winter Park. Spend days visiting museums, galleries, sculpture gardens, theaters, music venues, and if you’re lucky, arts festivals. The city’s commitment to enhancing awareness and visibility of the arts is seen everywhere, from traditional venues to unexpected yet powerful places.

Plan your trip around the schedule for the annual Bach Festival Society, another cultural gem housed on Rollins College in the Knowles Memorial Chapel. Hear the soaring sound of the Bach Festival Choir and Orchestra under the baton of Dr. John V. Sinclair, which has thrilled audiences worldwide, including in well-reviewed performances with the London Symphony Orchestra.

Venture to the north end of Park Avenue to explore the world’s most comprehensive collection of the works by Louis Comfort Tiffany, son of Charles Lewis Tiffany – founder of Tiffany & Co Jewelers. The Morse Museum of American Art showcases the designer’s famous leaded-glass lamps and windows, jewelry and other works.

Travel off the beaten path and witness beauty in the works of sculptor Albin Polasek at the Polasek Museum & Sculpture Gardens, which celebrate nature, unity of form and beauty of movement. The museum offers guided tours of the historic Polasek residence and chapel, and an outdoor sculpture garden.

Finally, discover the history behind Winter Park, central Florida’s original vacation community for Chicagoans seeking a warmer climate, at the Winter Park History Museum. The museum shares its efforts to preserve, promote and research the history of Winter Park through exhibits, educational programs and a free lecture series.

Other Adventures –

Visit Hannibal Square, a historic neighborhood two blocks west of Park Avenue. Enjoy al fresco dining, stylish home furnishings, fine art and unique gifts. While in the area, be sure to pamper yourself at some of the area’s top skin care spas and hair salons.

The Hannibal Square Heritage Center, established in 2007 by Crealdé School of Art, is a tribute to the past, present and future contributions of Winter Park’s historic African American community. The center hosts the award-winning Heritage Collection: Photographs and Oral Histories of West Winter Park, a permanent exhibition of over 100 pieces capturing the lives of Winter Park’s African-American community spanning the 20th century.

Mead Botanical Garden is located just a few miles from the downtown business district. It is a beautiful place to enjoy a lazy afternoon traversing the nature trails or dipping your feet in the freshwater ponds.

Kraft Azalea Garden is a serene 11-acre park just minutes from the Park Avenue shopping district. The park is bordered by beautiful Lake Maitland and offers benches for reading, picnicking or for simply enjoying a quiet relaxing time. The garden is beautiful year-round but be sure to visit in the months of January through March when the namesake flowers are in bloom.

10 Best Things To Do In Winter Park Florida

What was once an exclusive resort for the well-to-do in the 1800s is now a much-loved city whose magic has continued to draw in visitors from near and far. Winter Park is a suburb of the nearby Orlando, and it’s no surprise that visitors continue to flock here when in need of a little break from the big city. 

Known for its plethora of pristine parks and beautiful lakes, the town is a nature lover’s dream. There is also an impressive collection of museums, award-winning restaurants, and a great display of historic architecture. 

Whether you’re coming from nearby Orlando or further afield, Winter Park is a destination in its own right. There’s even an Amtrak stop here, making it a convenient day trip or weekend getaway. 

Here are some of the best things to do in Winter Park, Florida.

Take A Scenic Boat Tour

Take a ride through Winter Park’s beautiful chain of lakes on a scenic and historic boat tour. Operating since 1938, the city’s scenic boat tour is the perfect introduction to this stunning area. 

The tour takes you through the canals and lakes on a small pontoon boat, and a guide will point out all the noteworthy attractions along the way, including Rollins College, parks, museums, and opulent mansions. As you float, you’ll also see trappings of the wild area that this once was, with overhanging trees, lush vegetation, and scores of waterfowl and other wildlife. 

Tours run every day year-round, making this one of the best things to do in Winter Park no matter what time of year you’re in town.

Albin Polasek Museum

Even if you’ve never heard of Albin Polasek (chances are, you haven’t), a visit to the Albin Polasek Museum is one of the best things to do in Winter Park. 

This is part museum and part sculpture garden, and you can tour the artist’s former home before exploring the impressive sculpture garden out back. The home features original furnishings and over 200 pieces of Polasek’s work. The garden faces Lake Osceola, and if you’re lucky, you may be in town for one of the cultural events hosted here throughout the year.

Walk Around Downtown

No trip to Winter Park is complete without a stroll through the charming downtown area. Park Avenue is the town’s elevated version of Main Street, with boutique shops, upscale jewelry and furniture stores, and tons of restaurants.

As you peruse Park Ave, you’ll come across a number of cultural landmarks, including Rollins College, Hannibal Square, and Central Park – home to the famous Saturday morning Farmers Market. 

The downtown area is the perfect place to amble along without any plans in mind, and once you’re ready for a break, you can pop into a restaurant, stop for a glass of wine, or visit the gourmet chocolatier!

Charles Hosmer Morse Museum Of Art

While you’re downtown, be sure to check out the Charles Hosmer Morse Museum of Art. The museum houses one of the most comprehensive collections from Louis Comfort Tiffany, a renowned artist who dabbled in various mediums, including paintings, pottery, jewelry, and, most famously, glass. 

The newest exhibition features glass panels that were saved from the artist’s Long Island mansion, which burned down in 1957. There are many exhibitions inside this large museum, so be sure to block out a good chunk of time to discover the works of an artist whose life goal was “the pursuit of beauty.”

Mead Botanical Garden

One of the best free things to do in Winter Park, Florida, is visiting Mead Botanical Garden. This 47-acre garden is full to the brim with lovely landscapes, from colorful planters along paved paths to towering trees along scenic hiking trails. 

The wetland ecosystem plays host to a variety of creatures like turtles and waterfowl, and there’s even a butterfly garden on-site. This urban oasis sits a few miles from downtown Winter Park, but it’s easily accessible by foot or by car.

Enjoy A Day At The Central Park

Central Park sits in the heart of Winter Park, Florida and offers 11 acres for relaxing, gathering, and strolling. Of all the parks in the city, Central Park takes the cake in terms of location and foliage, with lovely purple wisteria blooming throughout the spring. There’s also a rose garden on the southeast end of the park, plus several fountains and lots of shady oak trees encircling the entire area. 

In addition to the inviting atmosphere, this lush setting also hosts a variety of events throughout the year, including a weekly Saturday farmer’s market, an autumn art festival, a Fourth of July celebration, and more. 

Sample Local Restaurants

Winter Park is chock-full of great restaurants, and what better way to get a taste of a place than by, well, having a taste of the food! 

Park Avenue is one of the best places to eat in Winter Park. In addition to the array of great shops, there are also tons of places to sit down and get some great grub. You’ll find everything from adorable coffee shops to swanky sit-down restaurants here, and there are tons of other options all around town to satisfy any craving. 

Visit The Shops

It should come as no surprise that a former swanky resort town has a great shopping district. Park Avenue is the main drag in town, and it’s hands down the best place to head if you want to shop ’til you drop. 

This upscale avenue is lined with both one-of-a-kind boutiques and well-known shops, selling everything from luxury home decor to cosmetics and everything in between. Once you’re all shopped out, you’ll find a variety of restaurants and cafes up and down the entire avenue.

Rollins College

Rollins College is often regarded as one of the most beautiful campuses in the country, so don’t miss your chance to see it while you’re visiting Winter Park. The sprawling campus overlooks Lake Virginia and boasts lovely historical buildings, several parks, and a free art museum. 

The Rollins College Museum of Art gets top marks for both quality and quantity – there are over 5,000 works in the collection in a variety of mediums from many different time periods, from the early Renaissance to contemporary works.

Kraft Azalea Gardens

If you’re looking for something a little more off the beaten path, make your way to Kraft Azalea Gardens. Situated just a mile north of downtown Winter Park, these lesser-known gardens feature trails through the public garden plus more paths through the park beyond. There’s also a small dock for fishing, a great egret rookery, and a photogenic temple styled with ancient Greece in mind.

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14 Best Things to Do in Winter Park (FL)

A cultural beacon for Greater Orlando, the picture-perfect city of Winter Park originated as a winter resort for the wealthy in the 1880s.

With its canals, lakes, moss-draped live oaks, and Mediterranean Revival architecture, I will never tire of exploring Winter Park.

You can do this on foot, wandering among cypress trees at lakeside parks, or on the water where the Chain of Lakes is linked by winding canals.  

There’s a stylish downtown area, next to Central Park, which has an active station on the SunRail line. From here you can get to Orlando’s Central Business District in a matter of minutes.

This green nexus point is the stage for events like one of the best farmers’ markets in Florida, and a nationally acclaimed art festival.

1. Charles Hosmer Morse Museum of American Art

Set downtown, the Charles Hosmer Morse Museum of American Art is home to one of the world’s most complete collections of pieces by Louis Comfort Tiffany (1848-1944). 

On show is a startling array of his leaded glass windows, jewelry paintings, pottery, enamels, furniture, and lampshades. 

Many of the items on display were salvaged from Tiffany’s home and studio, Laurelton Hall in Long Island, following a fire in 1957.

Maybe my favorite exhibit of all is the complete interior of the chapel for the 1893 World’s Columbian Exposition in Chicago. This space radiates opulence, with its brilliant mosaics and windows, in a Byzantine-Romanesque style.

2. Park Avenue

Lining the east side of Central Park is a truly elevated Main Street. In the shade of beautiful life oaks there’s a long line of upmarket independent businesses. 

Along this brick-paved thoroughfare are boutiques and an international array of restaurants. Most of these eateries have sidewalk tables, under awnings and that oak canopy. 

On Park Avenue and its side streets you can shop for luxury home decor, jewelry, designer clothing, cosmetics, fashion accessories, fine art, and more.

The mix of cuisines is equally diverse, whether you’re in the mood for smoothie bowls, New American, Turkish, Italian, French, Thai, Mexican, seafood, or steak.

The district is also bookended by two Winter Park cultural highlights. In the north is The Charles Hosmer Morse Museum of American Art, with its Tiffany masterpieces.

South, Rollins College, counts Fred Rogers among its alumni, and has been visited by presidents from Coolidge to Obama.

3. Central Park

A natural partner to Park Avenue, this leafy space hosts a variety of events and performances throughout the year. One of the recurring events is the Winter Park Farmers’ Market, which I’ll cover in more detail later.  

At other times, Central Park is just a pleasant place for a stroll or to relax with a good book or a good friend. There are fountains, tall old oak trees, and abundant flowers, especially in the rose garden in spring. 

Railroad tracks cross the park from north to south. Embedded in the greenery, Winter Park Station is served by Amtrak and SunRail commuter trains.

4. Albin Polasek Museum & Sculpture Gardens

In 1950 the Czech American sculptor Albin Polasek 1 879-1965 retired to Winter Park. Among his most famous works are The Spirit of Music (1923) in Chicago’s Grant Park, and The Yates Memorial, in Springfield, Illinois (also 1923).

Backing onto Lake Osceola, Polasek’s purpose-built home and studio was opened up as a museum in 1961. 

This is the only museum of its kind in Florida, keeping most of its original furnishings. The sculpture gardens are sumptuous, and complemented by the vistas over the water. 

There are around 200 works by Polasek on show, as well as pieces from his collection. For an educator’s perspective on his life and work, I’d recommend a guided tour. 

5. Rollins Museum of Art

Greater Orlando’s only teaching museum is on the campus of Rollins College. Founded in 1978, the Rollins Museum of Art has more than 5,000 works in its collection.

These holdings are wide-ranging, but have a few focal points, including contemporary art, American painting up to 1950, and European Renaissance art. 

When I paid a visit, the museum was in a period of sudden growth. There was a spellbinding display of new acquisitions by the likes of John Singer Sargent, Benjamin West and Thomas Cole. 

Some of the museum’s collection is also on show at the college’s Alfond Inn. Proceeds from this refined boutique hotel help fund scholarships.

6. Hannibal Square Heritage Center

Starting in the 1880s, the western half of Winter Park became home to the city’s African-American community. Early residents here worked on the railroads, or filled domestic service jobs in wealthy households. 

In 2007, the Crealdé School of Art opened a museum to document this aspect of the Winter Park’s heritage.

The focus here is the Heritage Collection: Photographs and Oral Histories of West Winter Park. This touching display has more than 100 pieces that shine a light on the African-American community. 

These are accompanied by a timeline, recording major events from the Emancipation Proclamation up to the election of Barack Obama in 2008.

7. Kraft Azalea Gardens

If you were to ask me how to close out the perfect day in Winter Park, I’d come to this little park at sunset. Just five acres, Kraft Azalea Gardens occupies a nub on the southeast shore of Lake Maitland. 

When the sun is low the thick stand of cypresses takes on a magical quality. It’s no shock that this park is a local spot of choice for golden-hour photo shoots. 

Come between late February and the start of June, and you should catch a glimpse of the egrets that nest in these giants.

8. Mead Botanical Garden

This magnificent botanical garden opened in 1940 in memory of the noted naturalist, Theodore Luqueer Mead (1852-1936).

For one thing, Mead’s friends needed somewhere to house his extensive collection of orchids. More than 80 years later, the Mead Botanical Garden is a joyous oasis concealed within the city.

Winding trails and boardwalks take you across wetlands and upland pine hammocks with some towering trees. There’s a creek, and a pond humming with life, from wading birds to turtles.

One spot I won’t soon forget is the butterfly garden, with a colorful array of flowering plants attracting pollinators.

9. Casa Feliz Historic Home Museum

One man who helped define Winter Park’s residential cityscape was the architect James Gamble Rogers II (1901-1990). 

He is most famous for the Florida State Supreme Court Building (1949) in Tallahassee. Yet, for much of the 20th century he worked in Winter Park, building homes in revivalist styles, ranging from Spanish Colonial to French Provincial.

A fine example of his early career can be seen at the Robert Bruce Barbour House, built for a local industrialist in 1932. Also known as Casa Feliz (Happy House), this has a rustic Andalusian style, fronted by a stately loggia.

Some interesting details I enjoyed on my tour—the Spanish terracotta roof tiles,the majolica-tiled courtyards, and the huge hand-cut beams in the living room’s vaulted ceiling.

A well-presented museum exhibit about James Gamble Rogers II had also just opened when I was here.

10. Winter Park Farmers’ Market

Held at Central Park West Meadow, the booming Winter Park Farmers’ Market is up there with the best in Florida.  The market happens on Saturdays from 8 AM until 1 PM, and packs a town’s worth of vendors into a relatively tight space. 

In addition to seasonal produce, you might find houseplants, herbs, sauces, wines, apple cider, maple syrup, seafood, pickles, cheeses, coffees, fresh bread, pet treats, and a wealth of artisanal crafts.

My one tip is to skip breakfast before coming, because there are some serious food trucks and static vendors. I’ve seen Indian street food, arepas, chicken pot pies, acai bowls, breakfast burritos, ravioli, Belgian waffles, and BBQ here.

11. Scenic Boat Tours

At the city’s lakefront parks, you’ll realize there’s a whole other side to Winter Park waiting to be discovered.

Edged with ferns, palms, oaks, cypresses, and elegant mansions the Chain of Lakes is connected by canals. These meandering waterways were built to convey lumber to a sawmill on the shores of Lake Virginia at the southern end of the chain.

For me, you need to get out onto the water to really get a feel for Winter Park. This can be done via the scenic boat tour, departing daily on the hour from 10 AM to 4PM. 

These tours have taken place since the 1930s, and are a gateway to a secret world, brimming with life. The Chain of Lakes is at once wild, with alligators and scores of wading birds, but also opulent. 

As well as the grounds of Rollins College, the grounds of numerous sprawling mansions frame the lakes and canals.

12. Winter Park Sidewalk Art Festival

Bringing hundreds of thousands of visitors from all over the country every year, the Winter Park Sidewalk Art Festival is my must-see event here. 

Held in Central Park in mid-March, the festival has been a fixture since 1960, and ranks among the best art fairs in the country.

The festival features a wide spectrum of arts and crafts, from paintings to jewelry, but also contemporary mixed-media.

Artists compete for awards in more than 60 categories, with prize money totalling more than $80,0000. The big one is the prestigious Best of Show. 

Live music and entertainment are woven into these three days, starting with a kick-off Friday night concert. There’s also a children’s workshop, and a complimentary bike corral throughout the festival.

13. Winter Park Golf Course

In typical Winter Park style, the city’s nine-hole public golf course is couched among live oaks, in a village-like environment. 

The holes at Winter Park Golf Course are traced by two churches, grand homes, a cemetery and the passenger railroad tracks.

Dating back to 1914, the course was renovated in the 2010s and is lauded as one of the best public short courses in America. I found this par-35 to be a real test, thanks to the small-ish greens, all guarded by sand traps. 

There are new fairways, greens and roughs, and a state-of-the-art irrigation system bringing the second-oldest course in Orlando into the 21st century.

14. Kayaking and Paddleboarding

If you want to navigate Winter Park’s Chain of Lakes in a more active way there are several outfitters and tour companies on hand.

Get Up and Go Kayaking, Otter Paddle Orlando, and Peace of Mind Kayak Tours all offer guided trips in this beautiful environment.

On these adventures you’ll have a little bit more freedom to check out wildlife, or linger in an especially picturesque area. This might be an oak-shaded canal, or a grassy bank with river otters playing.

Sunset paddle tours are available, and you can even head out onto these lakes after dark, on a glow-in-the-dark trip.

You may want ever more independence. In which case, Peace of Mind Kayak offers full or half-day rentals in Winter Park, with drop-offs.

14 Best Things to Do in Winter Park (FL):

• Charles Hosmer Morse Museum of American Art
• Park Avenue
• Central Park
• Albin Polasek Museum & Sculpture Gardens
• Rollins Museum of Art
• Hannibal Square Heritage Center
• Kraft Azalea Gardens
• Mead Botanical Garden
• Casa Feliz Historic Home Museum
• Winter Park Farmers’ Market
• Scenic Boat Tours
• Winter Park Sidewalk Art Festival
• Winter Park Golf Course
• Kayaking and Paddleboarding

20 Best Things to Do in Winter Park, FL

By: Author David Reeve

Posted on Published: February 4, 2023  - Last updated: June 24, 2023

Winter Park is a paradise for people looking for adventure, fun, and unforgettable memories.

Packed with stunning historic museums, beautiful theaters, and fun parks, Winter Park will enchant you with its old-world charm.

What’s more, this city is swarming with breathtaking lakes that offer relaxation and exhilarating outdoor activities.

And guess what?

You can enjoy the most memorable escapade by discovering the best things to do in Winter Park, FL, with our list below.

1. Charles Hosmer Morse Museum of American Art

445 N Park Ave Winter Park, FL 32789 (407) 645-5311

The Charles Hosmer Morse Museum of American Art is a gallery renowned for its art nouveau collection.

It houses the most extensive collection of Louis Comfort Tiffany’s creations.

Why You Should Go

Walking around the halls of this museum might be the most dazzling of the many unexpected pleasures Central Florida has to offer.

The world’s most extensive collection of works by American artist and designer Louis Comfort Tiffany is housed at this famous museum.

Along with his famous leaded-glass lights and windows, the Tiffany collection at the Morse also features the designer’s jewelry, pottery, paintings, and art glass.

Although you can take pictures without flash, do not bring tripods, monopods, or selfie sticks, as they are not allowed.

2. Albin Polasek Museum & Sculpture Gardens

633 Osceola Ave Winter Park, FL 32789 (407) 647-6294

The Albin Polasek Museum and Sculpture Gardens, or the Polasek, is a famous historic site on Osceola Avenue.

Want to see something spectacular but not sure what to do in Winter Park?

Visit Albin Polasek Museum and Sculpture Gardens for an enchanting experience.

The guided tour includes a short movie overviewing the property’s history and explaining the sculptures and inspiration behind Polasek’s creations.

Most of the sculptures are religious, and each one focuses on a distinct period of Polasek’s life while telling his tale.

There is always something fresh to view at the Albin Polasek Museum & Sculpture Gardens because the artwork is rotated seasonally.

Invite your family for a relaxing picnic day because this museum allows a small picnic lunch and food near the lake.

Related: Best Restaurants in Winter Park

3. Central Park

251 S. Park Avenue Winter Park, FL 32789 (407) 599-3397

Located on West Morse Boulevard, Central Park is an 11-acre park with fountains, a rose garden, seasonal activities, and festivals.

When looking for downtown spots to visit, go to the crown jewel of Winter Park: Central Park.

And if you love a relaxing stroll, you can easily add this place to your list of favorite things to do in Winter Park at night and day.

Numerous annual events and activities are held at this 11-acre park.

Our favorites include the Old Fashioned Fourth of July Celebration and the Winter Park Sidewalk Art Festival.

Thousands of people visit Central Park annually to admire its beauty, enhanced by its lovely fountains, planted planters, and oak tree canopy.

On the southern edge of the park, there is a magnificent rose garden that you can book for events.

And did we mention that it features some of the can’t-miss free things to do in Winter Park?

Forgot to bring picnic items?

You can visit the mall across the street for quick shopping.

Recommended Hotel Nearby: The Alfond Inn

Also See: Things to Do in DeLand, FL Tallahassee: Things to Do What to Do in Sarasota

4. Rollins College

1000 Holt Ave Winter Park, FL 32789 (407) 646-2000

Founded in 1885, Rollins College is a private college in Winter Park and is Florida’s fourth oldest post-secondary institution.

If you are looking for places to go today, visit one of the most beautiful campuses in America.

Early spring at Rollins College provides a gorgeous landscape that undoubtedly supports that statement.

The grounds are immaculately maintained, the buildings are colonial Spanish in style, and the lakeside views are stunning.

You can also visit the campus museum to learn new things and appreciate the cozy atmosphere.

Visit Burgerfi, a nearby comfort food restaurant, if you’re craving tasty and hearty snacks.

Recommended Hotel Nearby: Park Plaza Hotel Orlando – Winter Park

5. Kraft Azalea Garden

1365 Alabama Dr Winter Park, FL 32789 (407) 599-3334

Kraft Azalea Park and Garden is a famous 5.22-acre scenic public park located on Alabama Drive.

There’s nothing like Kraft Azalea Garden if you’re looking for unique things to see in Winter Park.

Be sure to search for the banyan tree while you are there.

Banyan trees have been planted throughout the tropics in botanical gardens and urban parks.

These trees are native to Sri Lanka and Pakistan and are revered by Buddhists and Hindus.

The banyan tree in Kraft Azalea Park is thought to be the northernmost banyan tree in Florida.

Additionally, it has withstood the frosts and is at least 70 years old.

Kraft Azalea Garden is a stunning park with enormous, centuries-old banyan trees and an abundance of birds.

So be sure to bring your cameras and capture those enticing sights.

Recommended Hotel Nearby: Hilton Garden Inn Winter Park, FL

6. Lake Virginia

Winter Park, FL 32789

Lake Virginia is a 223-acre public lake in Winter Park that offers scenic views and wildlife, including numerous fish and alligators.

Looking for fun things to do in Winter Park with kids?

Why not visit the famous and stunning Lake Virginia?

You can go boating, kayaking, and fishing, enjoy scenic views, and discover its abundant marine life.

Fishing and boating are fun activities on the lake.

However, the lake has alligators, so be careful.

They usually avoid humans but will attack when they feel threatened.

Recommended Hotel Nearby: Courtyard by Marriott Orlando Downtown

7. Casa Feliz Historic Home Museum

656 N Park Ave Winter Park, FL 32789 (407) 628-8200

Casa Feliz Historic Home Museum is a renovated Spanish farmhouse with traditional features, whitewashed brickwork, and well-kept grounds.

Visiting Casa Feliz Historic Home Museum is a must-visit spot in Winter Park.

Casa Feliz, a renovated mansion in the center of Winter Park, Florida, provides a brief respite from the contemporary world with its lovely interiors and picturesque gardens.

The Friends of Casa Feliz are responsible for running the Casa Feliz Historic Home Museum.

This nonprofit group promotes the community’s extensive architectural, historical, and cultural legacy by educating the public about it.

Visit on the weekends for a better experience because this stunning museum offers live music on Sundays.

Recommended Hotel Nearby: SpringHill Suites by Marriott Winter Park

Also See: Fun Things to Do in Palm Beach, FL Activities in Palm Coast

8. Rollins Museum of Art

1000 Holt Ave Box 2765 Winter Park, FL 32789 (407) 646-2526

The Rollins Museum of Art is the only teaching museum in the greater Orlando area and is situated on the Rollins College campus.

If you enjoy art, you must visit Winter Park’s Rollins Museum of Art,\.

The museum offers a continuous program as well as changing exhibits.

Additionally, they have a sizable permanent collection of more than 5,700 items that spans centuries and includes modern pieces and ancient art and antiquities specimens.

The Alfond Inn , a charitable boutique hotel run by the College, houses artwork from the museum’s collection and those on display.

Rollins Museum of Art is the indoor stuff to do when it’s raining or cold because it’s free and stunning.

However, to keep the museum running, donations are accepted.

9. Lake Baldwin Dog Park

2000 S Lakemont Ave Winter Park, FL 32789 (407) 599-3397

Located on South Lakemont Avenue, Lake Baldwin Park is a lovely, shady park on Lake Baldwin that spans 23.16 acres.

Lake Baldwin Park won’t disappoint pet owners looking for the ideal place to take their friends swimming.

This park is a 23.16-acre leisure space with a dog park and a beach that welcomes dogs.

In addition to swimming and tanning on the coast, Lake Baldwin Park offers many other fantastic activities.

If your pet is itching for some companionship, head to the dog park for a game of fetch or a playdate with some of their favorite canine friends.

Although the park offers a beach area, we recommend being careful around the waters as your animals may contact microscopic blue-green algae that are toxic to dogs.

Recommended Hotel Nearby: Home2 Suites by Hilton Orlando Downtown, FL

10. Mead Botanical Garden

1300 S Denning Dr Winter Park, FL 32789 (407) 622-6323

Located on Denning Drive, Mead Botanical Garden has a sizable, serene green area with various flower gardens, wildlife habitats, and pavilions.

Walking around the charming Mead Botanical Garden is one of the most romantic things to do in Winter Park for couples.

The 47.6-acre Mead Botanical Garden is a park with amenities like an amphitheater, a butterfly garden, a boardwalk, and a cycling route.

During spring and fall migration, this city park can be great for songbirds that rest on the bay marsh, stream, pond, and hardwood woodland.

You can see warblers, thrushes, vireos, tanagers, buntings, and flycatchers in April, September, and October.

This place is perfect for a picnic date, so be sure to bring snacks and other things you need.

Recommended Hotel Nearby: Hilton Garden Inn Orlando Downtown

11. Winter Park Historical Museum

200 W New England Ave Winter Park, FL 32789 (407) 647-2330

The Winter Park Historical Museum is a regional history institution located on New England Avenue.

The Association carries out this objective by offering a free guided tour to the people of Winter Park.

The Winter Park History Museum aims to investigate and preserve the rich history of Winter Park and its surrounding area.

This location is perfect for learning about the town’s history through free educational exhibitions, lectures, and outreach initiatives.

We recommend visiting on Mondays because they put on a free music show for children at 10 AM.

Recommended Hotel Nearby: Homewood Suites by Hilton Orlando North Maitland

Also See: The Florida Keys Activities Fun Stuff to Do in Marco Island

12. Hannibal Square Heritage Center

642 W New England Ave Winter Park, FL 32789 (407) 539-2680

Founded in 2007, The Hannibal Square Heritage Center is a community center operated by the Crealdé School of Art.

If you are looking for sights to see this weekend, visit the Hannibal Square Heritage Center.

It celebrates the historic African-American community of Winter Park’s past, present, and future contributions.

The center features community-produced public art projects and a revolving series of visiting exhibitions.

Additionally, they provide educational programs that examine the history of the African-American people, black culture, cultural preservation, and Southern folklore.

If you are feeling hungry, head to The Coop, a nearby restaurant specializing in Southern fried chicken.

Recommended Hotel Nearby: Sheraton Orlando North

13. Crealde School of Art

600 St Andrews Blvd Winter Park, FL 32792 (407) 671-1886

Opened in 1975, The Crealdé School of Art is a lovely non-profit arts organization offering classes and featuring local art.

Are you searching for creative activities in Winter Park?

Please stop by this art school.

The Crealde School of Art offers more than 125 visual arts classes and weekend workshops throughout the academic year.

For students of all ages, they provide classes in ceramics, sculpting, jewelry making, glasswork, printmaking, digital and traditional photography, painting, drawing, and more.

Don’t forget to visit the sculpture garden surrounding the school for a relaxing time and fresh air.

Recommended Hotel Nearby: Courtyard Orlando Altamonte Springs Maitland

14. Blue Bamboo Center For The Arts

1905 Kentucky Ave Winter Park, FL 32789 (407) 636-9951

Located on Kentucky Avenue, Blue Bamboo Center For The Arts is a non-profit center for the performing and visual arts in the city.

If you are looking for cheap activities to do near you, then pay a visit to Blue Bamboo Center.

There’s no better place to listen to live music than this art center in Winter Park.

This venue has a tiny stage, seating 140 people, and a recording studio in a former warehouse.

Their eclectic mix of regional and national performers will hold your attention and introduce you to various performing styles.

Grab some wine, beer, or popcorn offered by the venue while keeping yourself entertained and amazed by the live performances.

Recommended Hotel Nearby: Embassy Suites by Hilton Orlando Downtown

15. Cady Way Trail

Cady Way Trail Winter Park, FL 32792 (407) 254-9025

Cady Way Trail is a concrete pathway, which runs 7.2 miles between Orlando and Winter Park, and joins the Cross Seminole Trail in Seminole County.

The Cady Way Trail offers great connections between homes and commercial and shopping areas for bikers and pedestrians.

This path is one of the most popular over the weekends and early nights since it offers long shady segments that are ideal for riding in the spring and fall.

Bring a water bottle when you go out for a hike or a cycle.

There are plenty of benches and water fountains along the trail for resting and hydrating.

Recommended Hotel Nearby: Grand Bohemian Hotel Orlando, Autograph Collection

16. Breakthrough Theatre

6900 Aloma Ave Winter Park, FL 32792 (407) 920-4034

The Breakthrough is one of the most famous theaters in Winter Park that offers classes, seminars, concerts, and more.

You will love Breakthrough Theater if you are a music and theater arts fan.

The Breakthrough Theatre creates Mainstage plays of the highest caliber and a production and summer camp for kids.

They work with creative individuals and groups to promote understanding, acclaim, and the sharing of ideas.

Additionally, they provide unique seminars, workshops, movies, and concerts in addition to acting, dancing, voice, and improvisation classes.

Although there is little parking available, you can park at KeKe’s Restaurant or across the street on weekends and evenings.

Recommended Hotel Nearby: Fairfield Inn & Suites by Marriott Orlando East/UCF Area

17. Community Playground

255 S Denning Dr Winter Park, FL 32789 (407) 599-3397

The Community Playground, sometimes known as the “castle park,” is a sizable wooden structure where children can engage in imaginative play.

Looking for kid-friendly places?

Visit the Community Playground if you are also looking for nice places to visit in Winter Park with kids.

This playground, designed by nationally acclaimed playground designer Robert Leathers, is unique, including climbing structures, swings, and a slide.

Grab your lunch and snacks because this place offers a pavilion where people can eat or relax.

Recommended Hotel Nearby: Aloft Orlando Downtown

18. Baterbys Art & Framing (Also Known As Baterbys Art Framing & Furniture)

2054 State Road 436 N, suite 108 -112 Winter Park, FL 32792 (888) 682-9995

Located on State Road, Baterbys Art and Framing is a facility featuring breathtaking art collections.

When looking for cool attractions in Winter Park, Baterbys Art and Framing won’t disappoint.

Baterbys is one of the top resources in collecting art, with over 25 years of expertise in the sector.

This facility is home to over 1.7 million works of art, including works by some of the most well-known names in the art world and modern and local artists.

Feeling hungry?

Head to Steak n Shake, a nearby chain offering steaks and milkshakes, after your visit to Baterbys.

Recommended Hotel Nearby: Home2 Suites By Hilton Orlando Near UCF

19. Park Avenue Shopping District

110 North Park Avenue Winter Park, FL 32789 (407) 920-2043

The Park Avenue District is at the center of Winter Park’s downtown and is home to top-notch food, art, experiences, shopping, hotels, and unmatched culture.

Since 1887, Park Avenue District has served as the focal point of a luxurious winter resort, making it the ideal location for a tranquil stroll among its beautiful surroundings.

Experience one of Florida’s most distinctive and thriving towns as a destination for gourmet cuisine, fashion, and art.

The Park is also surrounded by a lush park that hosts events like concerts and art fairs.

This stunning district offers numerous events, so be sure to check out their website for information.

Recommended Hotel Nearby: Hilton Orlando/Altamonte Springs

20. Winter Park Scenic Boat Tour

312 E Morse Blvd Winter Park, FL 32789 (407) 644-4056

Located on Morse Boulevard, The Winter Park Scenic Boat is situated on Lake Osceola and offers hours of scenic guided boat tours around the lake.

If you are looking for the best things to do in Winter Park, FL, visit this scenic boat tour.

The boat tour offers hour-long, guided tours across three of the seven lakes and two thin-constructed canals on the peaceful Winter Park chain.

The abundance of wildlife and a wide range of thriving sub-tropical flowers are available to see or view on any given tour.

Another highlight of the scenic trip is the breathtaking views of wealthy estates and private mansions extending along the shoreline.

If you are a person that enjoys plant life or wildlife, be sure to bring binoculars or a camera that has excellent zoom features.

Remember, some plants and animals can be far away from the boat.

Recommended Hotel Nearby: Hampton Inn & Suites Orlando/Downtown South – Medical Center

Map of Things to Do in Winter Park

20 Best Things to Do in Winter Park, FL for [currentyear]

• Charles Hosmer Morse Museum of American Art
• Albin Polasek Museum & Sculpture Gardens
• Central Park
• Rollins College
• Kraft Azalea Garden
• Lake Virginia
• Casa Feliz Historic Home Museum
• Rollins Museum of Art
• Lake Baldwin Dog Park
• Mead Botanical Garden
• Winter Park Historical Museum
• Hannibal Square Heritage Center
• Crealde School of Art
• Blue Bamboo Center For The Arts
• Cady Way Trail
• Breakthrough Theatre
• Community Playground
• Baterbys Art & Framing (Also Known As Baterbys Art Framing & Furniture)
• Park Avenue Shopping District
• Winter Park Scenic Boat Tour

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Our mission is to serve the 50+ traveler who's ready to cross a few items off their bucket list.

6 Amazing Things To Do In Beautiful Winter Park, Florida

• Destinations
• United States

Located just seven miles north of the City of Orlando in Orange County, Winter Park’s 30,000 residents enjoy abundant outdoor spaces, a decadent Saturday morning farmer’s market, golf courses, and more museums than you would ever expect to see in such a small area. Created by several wealthy industrialists as their winter haven in the late 19th and 20th centuries, boating, museums, shopping on Park Avenue, and great food make it as delightful today as it was then.

I attended a press trip that included Winter Park. All the opinions herein are my own.

1. Scenic Boat Tour

The Scenic Boat Tour is a must-do and the perfect introduction to Winter Park. It is the oldest, continuously running attraction in the state of Florida since 1938! They operate seven days a week, 364 days a year (not Christmas). Peppered with jokes, facts, and wry asides, Skipper Don Brown’s a treasure trove of information along this gorgeous tour.

The Winter Park chain of lakes is connected by navigable canals created by Charles Mizell of timber fame to ship his product between six lakes (Maitland, Minnehaha, Mizell, Nina, Osceola, Virginia) in the mid-1800s.

The pontoon boats can’t have a roof or cover because the water levels on the lakes can be quite high during the wet season and there isn’t enough clearance for the boats to pass under bridges that dot the canals. Don’t worry, the lake view of all the historic homes make it well worth the trip with people kayaking around the pontoons.

Before you move too far along in our journey, though, it’s time for the first section of the historic shoreline to receive a shout-out. On the right side of the lake once stood the Old Seminole Hotel, the grandest hotel in the state of Florida. In 1886, maybe even the United States. It had 250 hotel rooms and a four-story tall observation tower from which you could see both Lake Osceola and Lake Virginia. Most impressive was its front porch, stretching 600 feet (that’s two football fields). Host to Presidents Grover Cleveland and Benjamin Harrison, many said that Rollins College and the Old Seminole Hotel brought “luxury to the edge of the Florida frontier.”

Sadly, the hotel caught fire in 1902 and burned to the ground.

Along the Scenic Boat Tour route, identify the “Resurrection Fern” and the “Dinky Dock,” an ecologically protected cypress with several homes designed and built by the famous architect, James Gamble Rogers.

2. The Charles Hosmer Morse Museum Of American Art

The Charles Hosmer Morse Museum was created by his granddaughter Jeannette Genius McKean and her husband Hugh McKean who had completed an internship with Louis Comfort Tiffany glass earlier in his life. First housed on the Rollins College campus, the collection outgrew that space, especially after the couple rescued as much as possible from Tiffany’s Laurelton Hall, Long Island, New York home that collapsed during a fire. It was the quick work of Jeannette and Hugh that saved so many panels of this precious work .

Along the tour, you’ll learn how many different mediums Tiffany found to work with. There are his lamps, of course, but also jewelry and furniture, the most astounding windows… explore how the light changes based on your position.

3. Albin Polasek Museum And Sculpture Gardens

Albin Polasek Museum and Sculpture Gardens , with over 400 bronze pieces, visible from the Scenic Boat Tour, remains a popular wedding venue and was donated by the artist’s wife following the death of this incredible Czech American talent in 1962.

However, the story of this museum and its foundation goes further still. When the Capen House was sold, the Polasek offered a safe haven for the original home. The new owners of the land the Capen House stood upon paid for the house to be split in two (called Fred and Ginger after the famous American dance team, Fred Astaire and Ginger Rogers), rolled down the hill, and floated across Lake Osceola to its current location. It took 45 minutes for the first half, according to our skipper, and 15 minutes for the second. Check out the YouTube video from 2010 where a drone covered the event. Movement across the lake starts at 1 minute and 42 seconds. 

Also found in Winter Park is the Rollins Museum of Art, the Winter Park History Museum, Casa Feliz Historic Home Museum, and Hannibal Square Heritage Center, with art galleries regularly hosting berry special events. If you’re interested in classes or summer art camp, check out the Crealde School of Art.

4. Kraft Azalea Gardens

While many visitors know to go to Mead Botanical Gardens, one of Winter Park’s best but little-known attractions remains Kraft Azalea Gardens . Popular for weddings, marriage proposals, and birthdays, it’s a magical place.

Located on Lake Maitland’s shores, this 5-acre public garden is free to enter and open year-round from 8 a.m. to sunset, with a boat dock, benches, and eight more acres of park to explore outside the garden. Relax at The Exedra, reminiscent of Golden Gate Park ’s Spreckels Temple of Music, wander the great egret rookery, or visit the northernmost Banyan Tree in the state of Florida.

5. Saturday Morning Farmers Market

Advertised as the “Number one produce and plant market in Central Florida,” Winter Park’s Farmers Market contains the city’s central park and lives up to the hype with a lovely, festive gathering place with vendors and shoppers reveling in the fresh, colorful produce, assortment of plants, baked goods, artisanal crafts, and other offerings. The City of Winter Park Sidewalk Art Festival is held in this same location each year. Details can be found here .

The train station stops nearby. They are still serviced by Amtrak.

6. Winter Park Shopping

Rifle paper company.

Winter Park’s Park Avenue provides ten tree-canopied blocks where you can wander around the 140 specialty shops, cafés, boutiques, and coffee shops. If you love stationery, you’ll want to stop at  Rifle Paper Company .

Peterbrooke Chocolatier

Interested in gourmet chocolate? Peterbrooke Chocolatier’s assortment of chocolate delicacies will tantalize your taste buds.   

The Impeccable Pig  

Need to find a chic outfit or trendy accessories? Check out The Impeccable Pig .

The Wine Room On Park Avenue

If you’re looking for a decadent restaurant experience with a special wine, cheese, and charcuterie (or to take as a gift to those at home), you’ll want to check out The Wine Room .

Winter Park Restaurants

As with most wealthy towns, Winter Park’s restaurants provide an embarrassment of riches. The sheer abundance of food found from The Glass Knife to the surprisingly good “college food” at Rollins College to the James Beard nominated chefs James and Julie Petrakis of The Ravenous Pig with special attention to great locations for vegans and husbands in need of “daycare,” there’s something for everyone in Winter Park.

The Glass Knife Cakes And Café

Executive Chef Kristy Carlucci and General Manager Bianca Hinksman recommend reservations at The Glass Knife if you’d like to eat on the porch on a typically busy day.  

Displays of season-specific items atop the glass display cases filled with decadent croissants, pastries, and cakes. Menus for brunch and beverages hang above rows of freshly made doughnuts.

Look closely at the long, butcher block table beneath the rectangular chandelier base and dropped pendant lights that line the entire 12-seat table. Therein lie several eponymous glass knives in multiple colors. The imperfections make them stunning.

Rollins College

Two places to eat on Rollins College’s Campus , the Boat House and the Student Cafeteria, Skillman Dining Hall, bring you to campus but you’ll stay to walk around and see why it highly ranks each year on the “ Most Beautiful College Campus ” list.

The college’s cafeteria is spacious, light, and inviting with some of the best views on campus across an Olympic size pool over Lake Virginia.

Dave’s Boathouse, a Star-K Kosher certified facility offers a dark wood finish large bar area as you enter from the lakeside with cozy dining and large tables to fit your party size.

If you’d like to stay on campus, check out The Alfond Inn . 

Ethos Vegan Kitchen

Enter Ethos ’ fun, festive atmosphere to a wide display of artwork, from the playful to the profound, you can choose to be seated or place a takeaway order behind the hostess station. You’ll be impressed with the “common” names in this vegan restaurant from sausage rolls and “chickun” or pork. Even bay cakes, their rendition of crab cakes, move quickly across the restaurant as happy plant-based diners eat their fill.

Fiddler’s Green Irish Pub And Eatery

Wives, take notice. Fiddler’s Green Irish Pub on Fairbanks Avenue declares itself:

“Winter Park’s oldest husband daycare center. If you need time for yourself, leave your husband with us. Packages, 1, 2, 3 pints available.”

It’s listed right under the Jameson sign, so it must be true.

Their bill of fare contains only two pages but is jam-packed with flavor and fun with plenty of Irish dishes and American favorites. Try the Irish egg rolls, boxty potato pancakes, shepherd’s pie, Irish stew, or the favored corned beef and cabbage.

The Ravenous Pig

James Beard nominated chefs James and Julie Petrakis have spent 16 years refining the customer experience at The Ravenous Pig . If you’re ready for a Florida twist, try the s’mores French toast (a thick, dark, brioche served with maple syrup, burnished marshmallow, and a dark chocolate mousse), pimento cheese fries, or fried chicken cordon bleu.

For a real treat, order the longboard of charcuterie that crosses the entire five-seat round-top table. Our server introduced us:

“Here we have soppressata, Saville Road cheddar, tête de cochon, and the lomo, the Toscano, and the camembert accompanied by a spicy IPA mustard as well as date jam, lamash, and salted walnuts.”

It’s impressive — a wine and cheese connoisseur’s dream.

Downtown Winter Park is close enough to downtown Orlando to make it an excellent day trip.

For more information on traveling to Florida , check out these articles:

• 17 Most Popular Florida Vacation Rentals (2022)
• 16 Florida Beach Towns Our Readers Love (2022)
• 8 Amazing Things To Do In Beautiful Tallahassee, Florida

Gail Clifford, MD, a physician for 30 years, has traveled to five continents and has visited all 50 United States. An avid traveler, she happily goes on new adventures, especially for birthdays. Multi-generational travel remains a treasured pastime. She currently divides her time between Ireland and the U.S. You can experience more from Gail on her site ABLE Travel & Photo .

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A menu of weekend pleasures in winter park.

By Peter Couture

Winter Park , just minutes from downtown Orlando, rewards both day-trippers and weekenders.

The best way to enjoy either type of visit is to use the menu method: Choose at least one museum, one restaurant and one attraction you must experience, then fill in any blanks as time and your wallet allow.

Winter Park, just minutes from downtown Orlando, makes for the perfect day trip.

- Julie Fletcher for VISIT FLORIDA

For the Day Tripper

A weekend stroll through Central Park in the city’s core — it sits across from the trendy shopping and dining of Park Avenue — is enough to put one in the mind of a Seurat painting: artists’ easels, young families and t'ai chi practitioners dot the landscape.

But take also the advice given to us by an enthusiastic and helpful staffer at the Winter Park Welcome Center , who tells visitors that if they have only one day to spend in town, then there’s one must-see attraction in The Charles Hosmer Morse Museum of American Art — “The Morse” to most everyone — and one must-do activity in the Scenic Boat Tour of the Winter Park chain of lakes.

Both the museum and the points of interest glimpsed on the boat tour owe their existence to the Northern tycoons who helped found the town as — what else — a winter retreat. Combine both activities, throw in lunch, and visiting families can still get back to their hotels in time for the kids to log some pool time.

For the Art Lover

Winter Park residents like to boast that their art-loving community has three museums and “two are cheap and one is free.” So true. If, like me, you think of lamps when you hear the name Tiffany, then The Morse will be nothing short of a revelation.

The museum holds the world’s most comprehensive collection of works by Louis Comfort Tiffany . Sure, the jewelry and those leaded-glass lamps are there, but the chapel interior from Tiffany’s installation for the 1893 World’s Columbian Exposition in Chicago is nothing short of awe-inspiring.

It’s hard for visitors not to reflexively remove their hats and speak in hushed tones while viewing it. Better yet, admission is not in Tiffany-price territory ($6 for adults, $5 for seniors and $1 for students with I.D.) 

In the mood to stretch your legs? Less than a mile from the Morse is the Cornell Fine Arts Museum , which is on the campus of Rollins College , the “oldest recognized college in the state.” Cornell exhibitions have ranged from thought-provoking looks at race to the rise of modernism.

So maybe you’d like to ponder what you’ve seen at the Cornell? Then take a stroll through campus. Rollins has been recognized by the Princeton Review for its beauty. (The reserved scooter parking for school president Grant Cornwell is a nice touch.) One other thing about the Cornell — it’s free, but donations are welcomed.

Nearby, the lakeside Albin Polasek Museum and Sculpture Garden welcomes you into the world of the acclaimed Czech-born American sculptor. The museum includes Polasek’s home, galleries and sculpture garden on Lake Osceola. For those who like visually adventurous works, the museum also brings in visiting exhibits in other mediums.

For the Hotel Lover

The gorgeous, Tuscan-designed Alfond Inn is a destination in and of itself. If you enjoy the finer things: art, luxury accommodations and contemporary cuisine, then the Rollins College-owned boutique hotel is a must — even if you don’t stay there. It contains The Alfond Collection of Contemporary Art , which draws works from the permanent collection of the Cornell that are displayed in the hotel’s lobbies and hallways.

We sipped cocktails near a large work by the Chilean artist Afredo Jaar that instructed in neon: “Be afraid of the enormity of the possible.” Indeed. A stay at the Alfond will make you a believer in that edict. Plus, the hotel has a philanthropic mission that benefits Rollins students.

The hotel’s restaurant, Hamilton's Kitchen , serves Florida-inspired cuisine. Even if you don’t dine there, appetizers from the restaurant — try the Hamilton’s Meatballs — make a fine accompaniment to a happy-hour drink on one of the Alfond’s scenic patios as you unwind from your Winter Park explorations.

In Winter Park, there’s room at the table for your best friend.

For the Culinary Tourist

And speaking of those who like to nosh, Winter Park salutes you. The eateries, which make an effort to stock their menus with local ingredients, run the gamut from the nationally acclaimed, such as The Ravenous Pig , to the laid-back Floridian fare of Atlantic Beer & Oyster .

The Pig should satisfy the meat-lover in your family; I can vouch for the housemade charcuterie. Even the Pig’s take on classic cocktails keeps the meat lover in mind: The Old Fashioned dunks a strip of candied bacon in the cocktail. Yum.

And there’s always a good chance that you’ll run into a food-tour group — as I did — as you explore Park Avenue, where it pays to explore the labyrinth of courtyards off the main strip. That’s how we found ABO’s excellent gulf oysters, local craft-beer selections and gulf oysters.

Elsewhere, the eclectic mix on and near the avenue include restaurants such as Bosphorous Turkish Cuisine and the Italian/Brazilian Braccia , both of which like to entice passers-by with free samples. Sadly, I never made it back to Park Station for the “Avenue’s best chicken-pot pie.” Next time.

A great perk on Park: Many restaurants set out water dishes for Fido, and the dog-watching may be even better than the people-watching for those dining at one of the many sidewalk tables.

For the Shopper

Start with the quaint and just-the-right-sized Winter Park Farmers’ Market , which is held on the site of the restored train depot — a historic landmark. The market takes place every Saturday, except on the third one in March when it's time for the popular Winter Park Sidewalk Art Festival .

The Avenue welcomes window-shoppers with a lineup of chic clothing and home-goods retailers such as Lilly Pulitzer, Lululemon Athletica and a unique Pottery Barn location in the former Colony Theater that retains the theater’s vertical sign.

And if you like nostalgia and crave just the slightest bit of touristy Florida, visit the Rocket Fizz Soda Pop & Candy Shop, where confections and kitsch collide. I especially liked the collection of international candies. Japanese Kit-Kats, anyone?

For the Florida Historian

As the Welcome Center advises, the Scenic Boat Tour should be on everyone’s agenda. The tours, which use open pontoon boats (remember the sun screen), leave on the hour from a dock just a pleasant five-minute walk from Park Avenue.

The hour-long tour navigates two narrow man-made canals that connect three of the local chain’s seven lakes and offer views of the estates of the wealthy founders (and occasional NBA star) who built lakefront estates. The canals that snake through residential neighborhoods are worth the price of the tour ($14) alone.

“If I should say quack-quack, what are you going to do?” our guide and captain, Wendell, asked as we cruised under some of roadway overpasses.

The answer of course: “Duck.” Wendell kept up a constant patter that was part local history and part comedic one-liners that made the tour a welcome throwback to Old Florida tourism.

Parting Advice

Winter Park makes for a rewarding detour off I-4 that has something for everyone, no matter your interest or itinerary.

PLACES TO REMEMBER

Winter Park

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25 Things to See, Tour, and Do In Winter Park

• October 2, 2019

1. Park Avenue Shopping District

The centerpiece of a lavish winter retreat since 1887, Park Avenue has long been the place for a relaxing stroll in elegant surroundings. Experience a unique destination for fine dining, fashion, and art in one of Florida’s most unique and flourishing communities. Bordered by a shady park that plays host to concerts and art festivals, Park Avenue is home to one-of-a-kind boutiques and well-known shops, sidewalk cafes and fine dining restaurants, as well as world-renowned art collections in the area’s museums tour.

Downtown Winter Park’s charm is magnified in the truly unique details: hidden gardens and side streets that are home to locally-owned shops, a farmers’ market that attracts both locals and visitors alike each Saturday morning, festive parades that mark the seasons and a scenic boat tour that cruises the canals between the City’s lakes overlooking the area’s most prestigious homes. Often called “Little Europe,” Park Avenue in downtown Winter Park is a year-round destination that is sure to charm visitors of all ages.

2. Charles Hosmer Morse Museum of American Art

The Charles Hosmer Morse Museum of American Art is home to the world’s most comprehensive collection of works by Louis Comfort Tiffany (1848–1933). The Museum’s Tiffany collection includes jewelry, pottery, paintings, art glass, leaded-glass windows and lamps, and the chapel interior the artist designed for the 1893 World’s Columbian Exposition in Chicago.

The newest wing of the Morse Museum, which opened in February 2011, provides long-term public access to a collection of art and architectural objects from Louis Comfort Tiffany’s celebrated Long Island home, Laurelton Hall. The Museum is open to the public Tuesday through Sunday throughout the year with the exception of some major holidays. To plan your visit and for more information, click  here .

3. Albin Polasek Museum and Sculpture Gardens

Founded in 1961, the Albin Polasek Museum & Sculpture Gardens is home to a fine art collection focusing primarily on American representational sculpture, with over 200 works by Czech-born American sculptor, Albin Polasek.

The museum also offers guided tour of the historic Polasek residence and chapel, an outdoor sculpture garden and a gift shop.  In addition, the museum hosts cultural events throughout the year, such as the Winter Park Paint Out in the spring and a Chamber Concert Series in the winter. The Museum is open to the public Tuesday through Sunday throughout the year.  To plan your visit and for more information, click here .

4. Winter Park Scenic Boat Tour

The Winter Park Scenic Boat Tour is an 18-passenger pontoon boat ride on the pristine Winter Park chain of lakes. The tour offers hour- long, guided cruises through three of the seven lakes and two man-made canals on the tranquil Winter Park chain.

Every tour guarantees plenty of swaying palms, towering cypress trees, lush ferns and a variety of flourishing sub-tropical flowers. You will also experience breathtaking views of opulent private homes and exquisite estates sprawling along the shores. Tour guides are sure to point out sights of Rollins College, Albin Polasek Museum & Sculpture Gardens, Kraft Azalea Gardens, and more. Tour are available for individuals and groups throughout the year. Learn more about the Winter Park Scenic Boat Tour and make your reservation.

5.  Culinary Excursion: Dining on Park Avenue

Park Avenue’s eateries offer something to suit every taste, especially foodies! This culinary utopia is home to over 40 restaurants, including everything from yogurt shops to award-winning fine dining. It also boasts a variety of gourmet food stores where you can find everything from savory spices to sweet treats.

Whether you are looking for brunch, lunch while shopping the Park Avenue District, or a special dinner with family and friends, Park Avenue provides a diverse mixture of cuisines. You’ll discover traditional French, Italian, Thai, Tex-Mex, Turkish and American dishes, as well as everything in between. There is even something to satisfy the vegan and vegetarian palate. Visiting later in the day? The area’s active culinary scene carries on late into the evening. Be sure to plan a stop at an upscale tavern or wine bar. View a listing of Park Avenue dining options .

6. Central Park

Central Park is the crown jewel of all the city’s parks. Conveniently located on Park Avenue in the heart of the downtown shopping district, this 11-acre park boasts shady oak trees, landscaped planters, sitting areas, open space and three beautiful fountains. There is even a rose garden at the southern corner of Central Park. The lush foliage and relaxing atmosphere make it the perfect environment for a picnic.

The park welcomes visitors to the city that arrive by train and hosts numerous events and activities throughout the year, including the Winter Park Sidewalk Art Festival, Winter Park Autumn Art Festival and the Olde Fashioned 4th of July Celebration. Enjoy this oasis of nature in the heart of Winter Park.  To learn more information about Central Park, click  here .

7. Winter Park Farmers’ Market

The Winter Park Farmers’ Market is held at the old train depot which has been restored into a historical landmark. The venue is a popular place for social events, weddings and small expos. However, it is most well-known for the weekly Saturday market.

The venue hosts the number one produce and plant market in Central Florida. The market takes place every Saturday morning from 7 a.m. to 1 p.m. and is a popular community-gathering place that provides fine produce, plants, baked goods and so much more. For more information about the Winter Park Farmers’ Market, click  here .

8. Rollins College

Located along the banks of Lake Virginia in the heart of Central Florida, the beautiful Rollins College campus encourages visitors to take advantage of Florida’s natural beauty and Winter Park’s history and charm. With its Spanish-Mediterranean architecture, lush grounds and gorgeous setting, Rollins was named one of the 50 Most Amazing College Campuses in 2011 by  The Best Colleges.

Feel free to tour across the lush landscaped 80-acre campus through the beautiful rose garden or along the Walk of Fame  containing more than 200 stones gathered from the birthplaces of influential cultural and historical figures. Take a relaxing walk on the  lakeside walking trail, visit the Cornell Fine Arts Museum or attend one of the many  cultural ,  sporting  or educational events offered by Rollins College throughout the year. For more information and to plan your visit to Rollins College, click  here .

9. Cornell Fine Arts Museum

Set like a jewel on the Rollins College campus overlooking beautiful Lake Virginia, the Cornell Fine Arts Museum offers visitors a sophisticated, intimate viewing experience in one of the nation’s most innovative college art museums. The richly diverse art collection of the museum boasts more than 5,000  works and is recognized as one of the largest and most distinguished collections in Florida.

Original and traveling exhibitions change seasonally and feature outstanding works of art for all tastes, from the early Renaissance to cutting-edge contemporary. The Museum’s original exhibitions are drawn from a broad range of paintings, prints, drawing and sculpture. The Museum is open to the public Tuesday through Sunday throughout the year. To learn more about the museum and to plan your visit, click  here .

10.  Casa Feliz Historic Home Museum

Overlooking the golf course in the heart of Winter Park lies the historic Casa Feliz, beautifully restored Spanish farmhouse designed by acclaimed architect James Gamble Rogers II. The exterior of the house and grounds provide a picture-perfect backdrop for weddings and parties. The rich textures of original Spanish roof tiles and whitewashed century-old bricks, a turret, a bell tower, and a heavy timber balcony detailed in colors of the Mediterranean. The lush landscaping—courtyards, sweeping oaks, and native plants contained by ancient clay amphorae add to the historic beauty if the restored farmhouse.

The rich detail of the interior of the house includes the living room’s vaulted ceiling of massive hand-hewn beams; the heavily carved European antiques accenting each room; a Majolica-tiled interior courtyard and fountain; arched doorways and a circular staircase, all evoking 19th century Spain.  Casa Feliz offers tour on Tuesday and Thursday from 10 a.m. – 2 p.m. and an open house on Sunday from 12 – 3 p.m. Other special events include Art at the Casa, Christmas at the Casa and the annual James Gamble Rogers Colloquium on Historic Preservation. For more information about Casa Feliz including upcoming events, click here .

11. Hannibal Square

Visit Hannibal Square, a historic neighborhood located along New England Avenue two blocks west of Park Avenue, between Virginia and Pennsylvania avenues. Enjoy al fresco dining, stylish home furnishings, fine art and unique gifts. While in the area, be sure to pamper yourself at some of the area’s top skincare spas and hair salons. For more information about historic Hannibal Square, click here .

12. Tour Winter Park History Museum

Explore the interesting history of Winter Park at the Winter Park History Museum. The Museum collects, preserves, promotes and researches the history of Winter Park and its surrounding area, and shares that history with the public through educational programs and the operation the museum. The museum is home to many collections of historical items relevant to the Winter Park community and also curates interesting exhibitions of Winter Park history. The Museum is open to the public Tuesday through Saturday, throughout the year. For more information about the Winter Park History Museum, click  here .

13. The Bach Festival Society of Winter Park

The auditioned all-volunteer Bach Festival Choir is the nucleus of the Bach Festival Society, with a membership of over 160 singers from all walks of life who share a love of great music.  Many members of the choir have music degrees or advanced musical training, serve as educators in the Central Florida area, or maintain active schedules as soloists in churches and other venues throughout the community. Others are simply brought to the choir by their love of music. To learn more about Bach Festival Society and upcoming performances, click  here .

14. Popcorn Flicks in the Park

The City of Winterer Park and Enzian collaborate to produce the “Popcorn Flicks” cinema series in Winter Park. The series features classic films for the whole family to enjoy. Popcorn Flicks are usually held on the second Thursday of each month at 8 p.m. (but may not start until sunset to provide an optimal viewing experience). The films are shown in Winter Park’s beautiful Central Park and are free and open to the public. Bring a blanket and picnic or stop by one of our fabulous Winter Park restaurants to grab some snacks to go! To learn more information and to see a list of upcoming flicks, click  here .

15. Mead Botanical Garden

It has been described as “an urban oasis, a refuge for wildlife, a  botanical garden emphasizing nature, sustainability and environmental learning, and a place for contemplation,  celebration, and recreation”. Mead Botanical Garden is located just a few miles from the downtown business district. It is a  beautiful place to enjoy a lazy afternoon traversing the nature trails or dipping your feet in the freshwater ponds. It is also an excellent venue for intimate gatherings to celebrate special occasions or as a pleasant setting for any group collaboration. For more information about upcoming events, programs scheduled in the garden or to make reservations click here .

16. Kraft Azalea Garden

Kraft Azalea Garden is a serene 11-acre park just minutes from the Park Avenue shopping district. The park is bordered by beautiful Lake Maitland and offers benches for reading,  picnicking, or for simply enjoying a quiet relaxing time. There are trails for short walks and a small dock that is ideal for fishing. The garden is beautiful year-round, but be sure to visit in the months of January through March when the namesake flowers are in bloom. Find out more about Kraft Azalea Garden by clicking here .

17. Winter Park Country Club Golf Course

The Winter Park Country Club is the second oldest golf club in the Central Florida area. The golf course opened in 1914. It makes its way through the downtown Winter Park area and provides a challenge to even the most experienced golfer. With its narrow, tree-lined fairways and postage stamp, bunker guarded greens, this course will provide a test for every shot in a golfers arsenal. Daily fees start at $12 to walk 9 holes for Winter Park residents and $14 to walk 9 holes for non-residents. For further information, call 407-599-3339 or click  here .

18. Shady Park

Shady Park, centrally located in historical Hannibal Square next to the community center, features park benches and a tranquil sidewalk pathway. It is perfect for reading a book or hosting a special community event. It also includes a “spray play” water feature and offers free admittance year-round. Restrooms are located in the Community Center. Kids have a place to dry off, but shirts and shoes are required for entry. To read more information about Shady Park, click here .

19. The Alfond Inn

The Alfond Inn contributes to Winter Park’s cultural and artistic reputation by housing an eclectic collection of contemporary art available for viewing by the public. The collection is an extension of the Cornell Fine Arts Museum at Rollins College and features over 240 paintings, photographs, sculptures and mixed media works commemorating various impacting points in history. On Fridays, be sure to take advantage of the free docent-led tour available at 1 p.m.

While experiencing these artistic proofs, feel free to indulge in the additional luxuries offered at the inn. Residents and visitors alike can dine in Hamilton’s Kitchen for holiday brunches and chef-inspired dinners or, attend special  events  like “Get Your Jazz On”. For more information about The Alfond Inn or to make a reservation, click  here .

20. Hannibal Square Heritage Center

The Hannibal Square Heritage Center was established in 2007 by Crealdé School of Art in partnership with residents from the Hannibal Square community and the City of Winter Park. It is a tribute to the past, present, and future contributions of Winter Park’s historic African American community.

The Heritage Center hosts the award-winning  Heritage Collection: Photographs and Oral Histories of West Winter Park , a permanent, museum-quality exhibition of over 100 framed, archival pieces that capture the lives of Winter Park’s African-American community spanning the 20th century, and the Hannibal Square Timeline which documents significant local and national events in African American history since the Emancipation Proclamation. The Heritage Center is open to the public Tuesday through Saturday throughout the year. For more information about Hannibal Square Heritage Center, click  here .

21. Cultural Walking Tour

Take a self-guided walking tour of the City’s historical treasures, including more than a dozen different sites. The tour route begins near the historic Winter Park Golf Club and heads south along Park Avenue. Calling attention to a variety of museums and landmarks along the way. The map indicates opportunities to head west to Hannibal Square, east to the public library and south to Rollins  College, home to the Annie Russell Theatre, Knowles Memorial  Chapel and Cornell  Fine Arts Museum. Download your guide by clicking here .

22. Alfond Boat House and Dinky Dock

Dinky Dock sits on Lake Virginia, a 224-acre lake in the Winter Park Chain of Lakes.  Now a public park, the area used to be the site of the depot for the Winter Park-Orlando Railroad.  Nicknamed the “Dinky Line” for its fragility, the railroad opened on January 2, 1889. The fare from Winter Park to Orlando was 15 cents.The trip measured six miles and took half an hour. The depot was removed in 1967. Hidden Gem Alert. Look for a monument, west of Dinky Dock on Lake Virginia, thats where the train station once stood.

Today, the dock offers boat access to the beautiful Lake Virginia and the Winter Park chain of lakes. Boaters launching at Dinky Dock may navigate through canals connecting five lakes. Lake Virginia, Lake Osceola, Lake Maitland, Lake Mizell and Lake Minneola.  Learn more information about Dinky Dock by clicking here .

If you are looking for an excursion,  Paddleboard Orlando  organizes a Venetian Winter Park Canal Tour through the Winter Park chain of Lakes and  FlyBoard Rentals of Orlando  launches flights, both departing from the Dinky Dock.

23.  Winter Park Public Library

The Winter Park Public Library offers a full range of services in its huge 33,000 square-foot facility. Open seven days a week, about 500 people use the library on an average day. A collection of over 280,000 books, audiobooks, music cassettes and CDs, videos, DVDs, and eBooks are available. You will even find the newest large-print books, fiction, and non-fiction books, and audiovisual titles which are displayed on the first floor. The Children’s Library offers a good selection of books, audiotapes, music, computer software, videos, and DVDs for young children, kids, and teenagers. The library offers a wide range of storytimes and special events for kids of all ages.

Library also offers computers for Internet, research, and word processing, as well as meeting rooms that are available to rent. Open to the public daily. For more information about the Winter Park Public Library, click here .

24. Winter Park Playhouse

The Winter Park Playhouse is Central Florida’s only professional musical theater dedicated to producing musical comedies, revues, and cabarets. Located just blocks from Park Avenue, an evening at the Winter Park Playhouse provides quality entertainment in an intimate setting.  Performances are offered year-round. The Mainstage series features seven light-hearted musical comedies and revues that are from Broadway or Off-Broadway. The Spotlight Cabaret Series is a monthly series featuring a different professional singer in an intimate setting. Visit the online box office to view what’s playing and to book your seat by clicking here .

25.  Special Events

Winter Park and its downtown area offer a robust events calendar, ensuring there is always something happening on the Avenue! Signature events like the Park Avenue Sip and Stroll, the Hannibal Square Wine Tasting, Taste of Winter Park, Spring and Autumn Art Festivals, and the Concours d’Eleganc e exotic car show delight both residents and visitors alike. Where traditional memories are made every holiday season. Hosting events including the annual Tree Lighting, Christmas Parade, and the lighting of the Tiffany windows in Central Park. Hosted by the Charles Hosmer Morse Museum. Your experience in Winter Park is not complete without joining in on the fun!

• Albin Polasek Museum and Sculpture Gardens , Charles Hosmer Morse Museum of American Art , Park Avenue Shopping District , Winter Park Farmers’ Market , winter park playhouse , Winter Park Scenic Boat Tour

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28 Best & Fun Things to Do in Winter Park (FL)

Winter Park is a beautiful city nestled in Orange County, Florida, United States. The city has a population of approximately thirty thousand, eight hundred and twenty-five according to the 2019 census.

Winter Park is an excellent destination to take the kids, as it features lots of museums, outdoor opportunities, a performing arts center & entertainment activities to enjoy.

There are numerous exhilarating attractions in the city, such as Albin Polasek Museum & Sculpture Gardens, Bulla Gastrobar, Casa Feliz Historic Home Museum, Cady Way Trail, the Winter Park Golf Course, Winter Park Farmers’ Market, Charles Hosmer Morse Museum of American Art, and more.

Without any doubt, Winter Park is a city any tourist will love to visit in Florida to explore all it has installed. Here are the top things to do in Winter Park, FL.

Things to Do in Winter Park, FL

1. mead botanical garden.

Mead Botanical Garden is an amazing natural spot with a spread-out green space that gives the environment picturesque views.

The garden is a paradise for those who love to spend the day around nature with a plethora of fauna and flora from different parts of the world.

Mead Botanical Garden features a large range of freshwater ponds, trees, wildlife habitats, and flowering gardens.

Of course, this garden is a great gateway from all the bustle and hustle in the world, a place to simply relax and reflect.

Mead Botanical Garden features many accessible trails that lead to the different natural environments with several animals.

Many spots in the garden are designated for picnics with several pavilions that may also be used for private events and functions.

Address: 1300 S Denning Dr, Winter Park, FL 32789, United States

2. Charles Hosmer Morse Museum of American Art

Charles Hosmer Morse Museum of American Art is a popular destination for art lovers in Winter Park.

As a world recognized museum, it features an exceptional collection of art nouveau with a unique mix of art, history, and culture.

Charles Hosmer Morse Museum of American Art is located in North Park and it houses the largest collection in the world of artworks by an American artist and designer Louis Comfort Tiffany.

The Louis collection includes paintings, pottery, Tiffany’s famed leaded-glass lamps & windows, and art glass with a beautifully restored Byzantine-Romanesque chapel interior.

Charles Hosmer Morse Museum of American Art showcases exhibits of American paintings dating back to the 19th century and early 20th century, American art pottery, and the arts and crafts movement.

Address: 445 N Park Ave, Winter Park, FL 32789, United States

3. Bulla Gastrobar

An important addition to your list of places to visit in Winter Park, FL, is the Bulla Gastrobar, a laid back and vibrant place to hang out with friends.

Bulla Gastrobar is a contemporary bar that offers tasty and original Spanish and Catalan tapas you can’t get elsewhere.

They also offer delicious, delectable meals made with high quality and freshly sourced local ingredients, which tells for its prominent taste and uniqueness.

Bulla Gastrobar offers an extensive food menu which includes Arroz Caldoso, Ham Croquettes, Coconut Flan, Seafood Paella Mixta, Patatas Bravas, Truffle Carbonara, Jamon Serrano, and Queso Manchego, Blueberry & Ricotta Pancakes, lamb chops and lots more.

The full service bar offers a wide variety of drinks such as bullfighter 12, Moscow mule 12, blueberry breeze, sangria, estrella galicia, Brooklyn lager, cigar city maduro, and more.

Bulla Gastrobar is open from Sunday to Wednesday from 11:30am-10pm and Thursday to Saturday from 11:30am-11pm.

Address: 110 S Orlando Ave #7, Winter Park, FL 32789, United States

4. Winter Park Farmers’ Market

If you want to go shopping in an energetic and a typical traditional environment, visit Winter Park Farmers’ Market .

Winter Park Farmers’ Market is open every Saturday from 7am to 1pm; the market is set up in an old refurbished train station, making it a unique place to shop.

The market provides freshly baked foods, plants, and fine produce with its limited space consisting of numerous vendors.

Winter Park Farmers’ Market features vendors like Annie Roo, Bailey Bleus Dressings, Beef Jerky by Jeff, Bren Creations, Captain Jo’s Fish Dip, Che Bella, Chef Edge Knife, Chez Vincent, Inc., Choose KOS, DOGgone Gourmet Treats, Doug’s Nutty Crunch, Florida Fresh Live Herbs and more.

Winter Park Farmers’ Market vendors offer authentic and flawless merchandise for affordable prices.

Address: 200 W New England Ave, Winter Park, FL 32789, United States

5. Lake Virginia

To your list of things to do in Winter Park, add a visit to Lake Virginia, the second largest lake after Lake Maitland, with a size of two hundred and twenty-five acres.

Lake Virginia is a popular destination for many people in the city because of its picturesque views with the views of beautiful mansions and Rollins College along its banks.

The lake is a perfect place for stand-up paddleboarding, water-skiing, and kayaking. Lake Virginia features a sandy beach, dock, and bit ramp; the lake’s northern shore is called Dinky Dock Park.

Lake Virginia is home to one of the most famous historical homes and estates in Winter Park called “Wind Song,” built originally in 1938.

Address: Winter Park, Florida 32789 United States

6. Cady Way Trail

For outdoor enthusiasts, add exploring Cady Way Trail to your list of fun things to do in Winter Park, FL.

Cady Way Trail is a 6.5-mile multipurpose rail trail found along the abandoned roadbed of the East Florida & Atlantic Railroad and goes across Baldwin Park.

This trail traverses a pastoral golf course and the beautiful homes, various parts of the trail consist of architectural elements.

Cady Way Trail is a popular trail for mountain biking, jogging, hiking, and other exciting recreational activities.

Address: Cady Way Trail, Winter Park, FL 32792 United States

7. Central Park

A beautiful 11-acre in Winter Park that offers visitors an amazing experience is Central Park . This park offers screenings of interesting films on every second Thursday night of the month.

Central Park is a reputable venue for many fun events throughout the year, such as the old-fashioned 4th July celebration and the annual Winter Park Sidewalk Art Festival.

The park is characterized by stunning landscaped planters, oak tree canopy, and fountains which attracts hundreds of visitors.

Central Park features a Rose Garden available for rental for small wedding ceremonies of less than twenty persons.

The park is large and well maintained, offering breathtaking views and making it a perfect place to spend the day.

Address: 150 W Morse Blvd, Winter Park, FL 32789, United States

8. Winter Park Distilling Company

If you’re looking for a place to hang out with your friends, add a visit to Winter Park Distilling Company to your list of things to do in Winter Park, FL.

Winter Park Distilling Company was established by Paul Twyford and Andrew Asher in 2010; it started as a small home-based business.

This locally owned distillery has flourished into the finest craft distillery in the State, which produces a wide variety of high-quality and handcrafted spirits.

Winter Park Distilling Company offers delicious vodka, bourbon, whiskey, and rum. In addition, they have an online shop that sells spirits and Winter Park Distilling Company items with guide tours available throughout the week.

Address: 1288 N Orange Ave, Winter Park, FL 32789, United States

Considering a Florida road trip, check out our guides on things to do in Punta Gorda  ,  things to do in Gainesville , and  things to do in Tallahassee  for a memorable trip .

9. Winter Park Playhouse

Winter Park Playhouse is a good addition to your list of things to do in Winter Park. It was established in 2002.

This is a professional musical theatre, and a non-profit organization focused on improving the quality of life for locals and introducing year-round professional musical theatre programming which inspires and entertains.

The theater can accommodate 123 persons and sets high standards in artistic integrity and recruiting competent artists.

Winter Park Playhouse offers a friendly atmosphere and great entertainment with fantastic customer service.

Address: 711 N Orange Ave, Winter Park, FL 32789, United States

10. Hannibal Square Heritage Center

Hannibal Square Heritage Center is operated by the Crealdé School of art as a community center dedicated to arts, crafts, and cultures made by Winter Park’s African-American community.

The center is situated in the historic neighborhood of Hannibal Square and hosts permanent and rotating exhibits of artworks.

Hannibal Square Heritage Center also hosts different educational programs, symposiums, and workshops that showcase local African-American artists’ past, present, and future contributions.

The center was founded by the Crealde school of art in 2007, and it houses a permanent museum quality exhibition of over a hundred frames that give insight into the lives of Winter Park’s African community from the 20th century.

Hannibal Square Heritage Center is a 3, 000 square foot facility available for rentals for any private and special events.

Address: 642 W New England Ave, Winter Park, FL 32789, United States

11. Bach Festival Society

Bach Festival Society was founded to honor the 250th anniversary of Johann Sebastian Bach’s Birth in 1935 at Rollins College.

They did that by presenting the composer’s orchestral and choral music to the public for their enjoyment, education, and pleasure.

Bach Festival Society comprises over one hundred and sixty singers from different backgrounds.

The society offers almost thirty ticketed performances, a high school choral festival, dozens of in-school educational programs, many community concerts, and more.

Bach Festival Society produces recordings and operates two community choirs reaching up to 50, 000 persons every year.

12. Crealde School of Art

The art center offers visual and three-dimensional art classes for adults and children, including other activities.

Crealde School of Art offers workshops and summer art camps, including visiting artists’ workshops series to the town.

These art classes and workshops are based on printmaking, photography, jewelry, painting, ceramics, glasswork, and sculpture

There are two large exhibition galleries featuring the works by local, national, and international artists, including the school’s students.

Address: 600 St Andrews Blvd, Winter Park, FL 32792, United States

13. Ocean Blue Galleries

Ocean Blue Galleries is an excellent addition to your list of fun things to do in Winter Park, FL.

They have been in the business for more than fifty years and have gained all the experience in the World of art. Ocean Blue Galleries has built a trustworthy reputation for networking and representing many of the Top selling & Most Collectible Artists from different parts of the world.

Ocean Blue Galleries is filled with unique artworks made by local, regional, and international artists, perfect for decor in homes and offices.

They are inviting everyone to come in and shop for their most loved art collectibles, instantly, you will become one of their continuous collectors.

Address: 202 S Park Ave, Winter Park, FL 32789, United States

14. Winter Park Public Library

For the book worms, here is something for you, add a visit to Winter Park Public Library to your list of things to do in Winter Park.

Winter Park Public Library is a 33, 000 square-foot facility focused on education and offering various essential services.

The library is home to a large collection of over 280, 000 items which includes the latest fiction & non-fiction, large-print books, audio-visual titles, eBooks, and audiobooks.

Winter Park Public Library also features a children’s library filled with different kinds of materials like videos, audio tapes, and DVDs for children of all ages.

The library offers Internet access, research, wood-processing, and printing, including hosting storylines and special events for kids.

Address: 460 E New England Ave, Winter Park, FL 32789, United States

15. Austin’s Coffee

Austin’s Coffee is dedicated to providing the best quality coffee beans imported and roasted right in the store.

They offer delicious and well-made cappuccino, and espresso in a comfortable and laid-back environment. Austin’s Coffee also offers an outstanding beer selection and sustainable wines.

Austin’s Coffee features independent films, live bands, live comedy, art shows, poetry, and several others to keep you in a festive mood.

They also serve a large food menu, including freshly baked goods, soups, sandwiches, and vegan & gluten-free options.

Austin’s Coffee offers you all you can possibly ask for, from delicious meals and drinks, to exciting live entertainment. 

Address: 929 W Fairbanks Ave, Winter Park, FL 32789, United States

Check out the top  things to do in Lakeland ,  things to do in Palm Coast , and  things to do in Clermont for a memorable exploration of Florida.

16. Ethos Vegan Kitchen

Whether you’re celebrating or just want to enjoy a delicious meal, visiting Ethos Vegan Kitchen is one of the best things to do in Winter Park.

Ethos Vegan Kitchen is a fantastic vegan restaurant and bar that offers a laid-back atmosphere with a beautiful interior.

The restaurant features a cozy outdoor courtyard, wooden beams, exposed brick walls, and wooden beams. Ethos Vegan Kitchen’s full service bar offers a wide variety of craft brews and an impressive selection of New World wines.

Ethos Vegan Kitchen offers a variety of gourmet sandwiches, Blackened Tempeh, Yo Mama’s Lasagna, meat-free shepherd’s pie, BBQ Pork Sandwiches, banana peppers, pecan-encrusted eggplants, Coconut Curry Wrap, pizza with broccoli, and more.

They offer drinks like North coast, pinot grigio, pinot noir, hot tea, milk, rowdy bush, carson Scott, latte, juice, boylan fountain drinks, cold brew, burnside, and more.

Address: 601-B S New York Ave, Winter Park, FL 32789, United States

17. Adjectives Market

Shopping at Adjectives Market should be added to your list of things to do in Winter Park, especially with your friends and family.

Adjectives Market is a 50, 000 sq ft facility and the number one spot to shop for beautiful items for your homes or offices.

The mall showcases a vast collection of contemporary and restored antique home decor and antique furniture.

Adjectives Market features accessories, gifts, jewelry, fashion, vintage records, handcrafted jewelry, unique gifts, historic memorabilia, vintage designer handbags, and more.

This is a perfect place to visit and increase your curiosity with exceptional ideas brought to life by artists who love stylish accessories, home decor, and furniture.

Address: 130 N Park Ave, Winter Park, FL 32789, United States

18. Rollins College

Rollins College was founded in 1885 as a private liberal arts college that offers different graduate programs.

This college features one of the most beautiful campuses in the country, and it is a four-year, re-educational institution with sixty undergraduate and graduate majors and minors.

Rollins College offers special courses like The science of Sustenance, strategies for Changemakers, and Job Market Boot Camp.

When the President cancels classes due to the weather, the college hosts Fox Day every spring; students are allowed to go to the on-campus swimming pool or one of the many nearby lakes for relaxation.

Address: 1000 Holt Ave, Winter Park, FL 32789, United States

19. Albin Polasek Museum & Sculpture Gardens

Albin Polasek Museum & Sculpture Gardens should be on your list of top things to do in Winter Park, FL.

It occupies a three-acre land space on Osceola Avenue and was established in 1961 to showcase the works of Albin Polasek, the famous Czech Sculptor.

Albin Polasek spent almost all his life in Florida, and the museum was formerly his home & studio for over fifty years.

Albin Polasek Museum & Sculpture Gardens houses a fine art collection of American figurative sculptures consisting of more than two hundred works.

The museum is open for guided tours to everyone, both visitors and locals, as a historic residence and adjacent chapel which gives guests an insight into the sculptor’s life.

Albin Polasek Museum & Sculpture Gardens also features a beautiful outdoor sculpture garden where several cultural events are held throughout the year, such as the Winter Park Paint Out and a Chamber Concert Series.

Address: 633 Osceola Ave, Winter Park, FL 32789, United States

20. Alfond Inn

For a peaceful and memorable stay during your vacation, add Alfond Inn to your list of things to do in Winter Park.

Alfond Inn is a beautiful boutique hotel well designed and constructed with gorgeous artworks all over the hotel.

This hotel is an extension of the Cornell Museum of Fine Arts, consisting of charming luxury rooms with mind-blowing artworks.

Every room is well furnished with comfortable beds, soft sofas, large flat-screen Tv, microwave, coffee maker, air conditioner, and much more.

Alfond Inn features the renowned Hamilton’s Kitchen, which serves delicious and hearty meals to visitors during their stay.

The facility features several essential amenities such as a luxury rooftop pool, meeting & event space, lively courtyard, self-service bar, free wifi network, and more.

Address: 300 E New England Ave, Winter Park, FL 32789, United States

21. Kraft Azalea Gardens

Kraft Azalea Gardens is a gorgeous public park in Winter Park established in 1938 by George and Maud Kraft.

The park consists of numerous shades of large cypress trees with a lovely grassy space that offers a tranquil and romantic ambiance.

Kraft Azalea Gardens features a scenic Greek exedra monument with a semicircle of white colonnades and cypress canopies.

There is a small nice dock for fishing on the lake; the park also consists of the northern-most banyan tree in the state.

Kraft Azalea Gardens is known for its bright and colorful display of blooming flowers, especially from January to March.

Several picnic spots are perfect for an intimate moment with your loved ones as you enjoy the dramatic environment.

Address: 1365 Alabama Dr, Winter Park, FL 32789, United States

22. Casa Feliz Historic Home Museum

Casa Feliz Historic Home Museum, a unique structure often referred to as the Robert Bruce Barbour House.

It is an incredibly refurbished Spanish farmhouse that overlooks the golf course in the center of Winter Park.

Casa Feliz Historic Home Museum was designed by James Gamble Rogers, a popular architect, and the house is one of the most beautiful architectural structures.

The building was erected using Mediterranean hues, a turret, a wide timber balcony, Spanish roof tiles, a bell tower with interiors made with arched doorways, a majolica-tiled interior courtyard, hand-carved European antiques, a spiral staircase, and more.

Casa Feliz Historic Home Museum is an excellent place for special occasions with the lush gardens surrounding it.

Address: 656 N Park Ave, Winter Park, FL 32789, United States

23. The Winter Park Golf Course

Playing golf at the Winter Park Golf Course is one of the fun things to do in Winter Park and a perfect way to spend the day.

Winter Park Golf Course was officially opened in 1914, making it the second-oldest golf club in Central Florida.

It is a nine-hole public golf course of 2480 yards par 35, surrounded by the city’s neighborhood homes, the city’s streets, two churches, and a cemetery.

Winter Park Golf Course is great for players of different skill levels, offering them a fun and challenging game.

Address: 761 Old England Avenue Winter Park, Florida 32789 United States

24. Hunger Street Tacos

Hunger Street Tacos is a popular spot for foodies; they serve authentic Mexican street fare using special recipes.

The restaurant walls are adorned with artworks and murals by the Lapiztola Collective, founded by designers Rosario Mtz & Roberto Vega and local artists Liseth Amaya & architect Yankle Balderas.

Hunger Street Tacos consists of a lovely shaded patio with seating for outdoor dining in a clean and comfortable environment.

The restaurant offers vegetarian, vegan, and gluten-free options, ensuring that every meal is made with fresh and healthy ingredients.

They serve meals like quesadillas, enchiladas, tacos, burritos, chorizo, tacos stuffed with seared brisket, scrambled eggs, Campechano, Esquites, Birria Machete, Papas Aplastadas, Chips and Salsa, and more.

Address: 2103 W Fairbanks Ave, Winter Park, FL 32789, United States

25. Cornell Fine Arts Museum

Cornell Fine Arts Museum is located on the campus of Rollins College, which overlooks the tranquil waters of Lake Virginia.

The Museum houses a distinct collection of more than five thousand artworks and is deemed one of the nation’s most innovative college art museums.

Cornell Fine Arts Museum’s extensive collection consists of centuries-old objects, starting with ancient art and artifacts.

The Museum also features an education gallery specifically for the young ones with hands-on activities to motivate creativity and logical skills.

Cornell Fine Arts Museum comprises a museum shop that sells art books and museum-published titles. In addition, the museum hosts different programs and other art related events.

26. Shady Park

Shady Park is in historical Hannibal Square, close to the community center. The 3.28-acre Park has benches and a peaceful sidewalk pathway. 

The tranquility of this Park makes it perfect for reading a book or holding a special community event. 

Shady Park is also an excellent destination for taking your kids for a simple stroll in the afternoon. 

The playground equipment in this park will keep kids occupied. Their spray ground is another exciting feature. 

Address: 721 W New England Avenue, Winter Park, FL 32789, United States

27. Aloma Bowl

Aloma Bowl Entertainment Center, in the center of Winter Park, has been in this community for over 40 years. 

Aloma Bowl is fun for the entire family, with high-quality services and numerous amenities.

Besides having the best bowling, you can play in their arcade, flex your skills around the billiard tables, or watch the game on their enormous screens. 

Aloma Bowl’s full-service grill offers all your best bites. They host thrilling events every week, such as live music, trivia, karaoke, and much more. 

Visit them or book their venue to host your party, team building, or corporate event. 

Address: 2530 Aloma Ave, Winter Park, FL 32792, United States

28. Peterbrooke Chocolatier of Winter Park

Peterbrooke Chocolatier of Winter Park is the deluxe confectioner in Florida. This chocolate store is locally owned by a couple, Kevin and Jami Wray. 

When you visit this chocolate shop, you will feel like a kid in a candy store. 

Within the shop, you will discover hand-dipped strawberries, chocolate-covered pretzel rods, chocolate-dipped cookies, and more mouth-watering chocolatey goodness. 

Other yummy goodness includes traditional favorites like hand-made caramel, decadent truffles, scratch-made marshmallows, cookies, and potato chips. 

Chocolate lovers should include sampling chocolate at Peterbrooke Chocolatier of Winter Park on their list of top things to do in Winter Park, FL.

Address: 300 S Park Ave, Winter Park, FL 32789, United States

Are you considering exploring Florida, here is a guide on things to do in Boynton Beach ,  things to do in Homestead , and  things to do in Ocala  for a fun vacation

Plan a Trip to Winter Park

Winter Park will cater to all your adventures, offering you a chance to create new and unforgettable memories.

It is a vibrant city with countless attractions like parks, galleries, eateries, museums, lakes, markets, golf centers, distilleries, and much more.

There are lots of things to do in Winter Park, start planning your trip!

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Why you should consider visiting Winter Park, Florida, an easy day trip from Disneyworld

January 1, 2020 by Steve Ertrachter 3 Comments

Most travelers thinking about visiting Central Florida, think Disneyworld. Only twenty minutes from Downtown Orlando is the charming city of Winter Park. Winter Park is not widely known but should be. It feels like the best of many American cities mixed together with its beautiful streets, cozy boutiques, beautiful campus, and walkable downtown area. I hope that you’re inspired to visit Winter Park!

This blog was just updated with new updates and including another great overlooked nearby city, Altamonte Springs.

If you’re looking to get away from the insanity of Disneyworld, Winter Park is a great destination that is a 45-minute drive from Disneyworld and a great place to relax away from the parks. If you’re visiting Disney as well as Orlando for a few days, this is a good area to stay in near Disney if you’re looking for a boutique hotel with character although I recommend checking Rollins College’s calendar to avoid big college holidays.

*Photos courtesy of City of Winter Park Communications Department

• 1 Art Museums in Winter Park
• 2 Take a scenic boat tour of the many lakes
• 3 Rollins College
• 4 Old Train Station Depot / Winter Park Farmer’s Market
• 5 Kraft Azalea Garden
• 6 Bookstores
• 7 Pottery Barn
• 8 Where to eat in Winter Park
• 9 Altamonte Springs
• 10 Have you been to Winter Park?

Art Museums in Winter Park

Winter Park offers great cultural activities in part due to the Charles Hosmer Morse Museum of American Art . This is a great stop on a rainy day or even on a sunny day. This museum has a vast collection of Louis Tiffany’s glass windows and other artworks. There were rooms full of paintings, furniture, and other ceramics. I spent nearly one and a half hours and was amazed by the huge collection. There is a small admission price, but it’s worthwhile.

I also enjoyed the Albin Polasek Museum and Gardens as it offers fantastic sculptures crafted by Alkin Polasek. Albin Polasek was a multi-talented Czech sculptor who lived in Winter Park. The gardens were really nice to wander around.

Cornell Fine Art Museum at Rollins College is a great free art small museum that has 3-4 different new exhibitions every year and a wonderful permanent eclectic collection. I was impressed by the permanent collection as it includes Matthew Brady’s photographs of Lincoln, Dutch masters, and modern masters.  It should be added to your must-see list when visiting. 

Hannibal Square Heritage Center in Hannibal Square displays the history of the African American community in Winter Park. There are photographs of the residents in the 20 th century and important events since 1865 in the area.  Admission is free. Walks are offered by the Center as this was an important center of African Americans in Central Florida. 

There are a large number of art galleries in Winter Park. While each gallery has a niche; modern art is prominently displayed at the Ocean Blue Gallery. The galleries offer many different forms of media for sale from inexpensive to expensive. Don’t be afraid to step inside even if you don’t intend on buying something!

Take a scenic boat tour of the many lakes

One popular activity that I can recommend is the scenic boat tour that departs each hour for the various lakes around Winter Park! The lakes are full of fancy homes although the ride itself is quite relaxing and intimate. The ride passes through seven lakes and it’s a great opportunity to see wildlife. Be sure to bring a hat as well as cash. Arrive early to find parking.

Rollins College

Rollins College has been ranked as the most beautiful campus in the USA. It truly is stunning and straight out of a movie. The buildings have a Mediterrean feel and you can visit the campus for free.

Old Train Station Depot / Winter Park Farmer’s Market

There is a great old restored train station in the middle of the park dating back to 1913. Today, it is used as a Farmer’s Market and open every Saturday in the mornings. I always like to support local farmers and there’s something about enjoying freshly picked produce!

Kraft Azalea Garden

Kraft Azalea Garden was a great public garden next to Lake Maitland. The view is beautiful and relaxing.  It should be visited on a sunny Florida day. 

There are several independently run bookstores in Winter Park. I visited both the Writer’s Block Bookstore and the New Leaf Bookstore . Both have a great selection of books, including autographed copies of books.

Pottery Barn

Yes, Pottery Barn. I was amazed by the history of this building since it was formerly the Colony Theatre in the 1940s and still has the art deco marquee feel. If you like architecture, it was worth a stop.

Where to eat in Winter Park

If you’re looking for a great meal away from the crowds of Orlando, Winter Park is a great destination for a good meal. If you are in the mood for Middle Eastern food, Bosphorous Turkish Cuisine i s a great choice. It is always popular with the locals and moderately priced. Great kebabs and hummus are served here.

The Winter Park Fish Company offers really fresh fish for lunch and dinner. The prices are moderate and offer great value. There are many vegetarian and American restaurants so whatever you like, you are in business.

For coffee and tea, Barnie’s Coffee & Tea is deservedly very popular. Great coffees and teas are sold all day. Their flavored coffee was fabulous. They also serve an excellent breakfast and lunch, including tacos and salads (which I recommend!). There are many other coffee and tea places around the town if you want to sit and enjoy the downtown area.

Altamonte Springs

Just 10 minutes away by car is a town that is known for its large Mall located at Uptown Altamonte. I recommend visiting Cranes Roost Park as it offers numerous events throughout the year and has fountains and music concerts. Café Murano is a great Italian restaurant that moderately priced and remains very popular with local residents. The chicken dishes were great. A real local favorite is TooJay’s Deli that offers New York deli food. I thought that I was home after trying their platter. 

The gem of Altamonte Springs is Lake Lotus Park. Admission is free and consists of 120 acres of wetlands, woods, and nature. Be sure to take the one-mile walk on the boardwalk as you see native plants and encounter true nature. The park is only open from Thursday through Sunday. Be prepared to park across the street and take a bumpy ride in a wagon.

Have you been to Winter Park?

• 10+ great day trips from Orlando for culture and history
• Clermont: Another charming town near Orlando
• Where to see manatees in Florida

About Steve Ertrachter

New Yorker–born and raised. Lover of tennis. Curious. Frugal and independent traveler who believes that travel yields an understanding of different cultures. 10% of the magic behind Wanderlustingk.

Reader Interactions

February 28, 2019 at 6:32 pm

I love this article which has so much information. Makes me want to head over to Winter Park now.

April 7, 2022 at 1:37 am

I find myself without a traveling partner but hope to venture out on my own. Winter Park seems to be a good solo trip. ( I live in Gainesville, maybe three hours away.) I would love to stay in a very nice hotel, hopefully with charm. A bed and breakfast would be good. Do you have any suggestions? Also, is the cruise around the lake a yearly thing? Also again, LOL, When you travel are you able to get in some tennis, even if you don’t have a tennis partner? Thank you for your reply. Jane

April 21, 2022 at 2:39 pm

It’s Florida, so tennis is possible year-round! Maybe asking for the local tennis club is the best thing as I am sure you’ll find some players! WHen staying in Winter Park, I stay with family, so I cannot recommend a B&B, but I am sure that there are some good options!

The cruise around the lake takes place the whole year! Hope you have a great trip!

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The 12 Best Things To Do In Winter Garden, Florida

This town near Orlando is brimming with quaint, walkable delights.

Kelsey Glennon is a travel writer & photographer with experience traveling to over 50 countries. She’s a Floridian and solo female traveler covering luxury hospitality, interior design, sustainability, and lifestyle.

Things To Do

Where to eat, where to stay.

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An Orlando suburb in the backyard of Disney World, Winter Garden is the real life “Main Street USA.” Here you'll find locals enjoying a stroll down oak-shaded Plant Street, or dining on gourmet farm-to-table meals at locally-run restaurants. Winter Garden’s charming downtown, defined by a wisteria-draped bike trail piercing through its center, is on the National Register of Historic Places. It’s the perfect place to take a slow stroll and pop in the diverse small businesses that thrive in the shadow of the theme park giants.

From art galleries to regional theatre to fresh Florida dining, Winter Garden is a microcosm of rich culture and old Florida charm. It makes a quaint home base for travels and adventures around Orlando.

Whether you're looking for a weekend retreat or a day trip, here’s how to make the most out of your stay in Winter Garden, Florida.

Courtesy of Garden Theatre

Explore Downtown

Start your day in the heart of Winter Garden on Plant Street, where you'll find a picturesque downtown lined with quaint shops and cafes in historic buildings. Don't miss learning about West Orange County history at the Winter Garden Heritage Museum , the key to understanding the town's rich past rooted in citrus and rail. For the history enthusiasts, you can book historic guided walking tours here.

wghf.org , 21 E Plant St, Winter Garden, FL 34787

Hit the Biking Trail

For a more active day, rent a bike at Wheel Works and embark on a leisurely ride cycling the West Orange Trail . The 22-mile-long trail is repurposed from old rail road tracks and runs through towns, parks, and countryside throughout Central Florida. You’ll share the trail with joggers, skaters, and even pro cyclists training for their next distance race. The West Orange trail connects Florida’s coast-to-coast cycle path.

Meander the Farmers' Market

Shop at the Winter Garden Farmers Market on Saturdays in the downtown pavilion. It's one of the best in Central Florida, offering fresh produce, handmade goods, and a bustling atmosphere with live music. It’s a great spot to pick up Florida honey, fresh bread, local art, a bouquet of flowers, and organic local produce from The Farmacy . Don’t leave without securing a souvenir from the A.B. Newton & Company tent, a local print and design company famous for their regional city map prints.

Indulge in the Arts

When not performing at Disney World, local entertainers stay creative putting up well-produced Broadway shows at the historic Garden Theatre . The vintage-style theatre also hosts classic movie nights and touring productions. For a look at local visual art, stop in SoBo Art Gallery in the town’s turn-of-the-century fire station.

For such a small town, Winter Garden is a diverse, foodie hub in Central Florida.

Courtesy Lee & Rick's Oyster Bar

Grab a Filling Breakfast

Start with a breakfast of French pastries at Rosalie French Cafe . If their Parisien patio is too crowded with early morning cyclists, Three Birds Cafe and Axum Coffee are just across the cobblestoned street.

Hit up a Local Lunch Spot

For lunch, grab hearty American fare at The Hangry Bison , or join the locals for sandwiches, flatbreads, and burgers at Pammie’s Sammies .

Enjoy a View

Most dining venues in Winter Garden have sidewalk dining to enjoy Florida’s nice winter weather, but it’s on the rooftop of The Whole Enchilada where you’ll catch a breeze and the best view of the busy main street. 

Cozy up at a Local Legend

Lee & Rick’s Oyster Bar has been a Winter Garden legend since 1950. The unadorned local haunt serves up fresh oysters and has a loyal following of local regulars.

leeandricksoysterbar.com , 5621 Old Winter Garden Rd, Orlando, FL 32811

Hit the Town for Dinner

For dinner, indulge in a The Chef’s Table at the Edgewater, Winter Garden’s historic hotel. This intimate restaurant offers a three-course prix-fixe menu that changes regularly, featuring the fresh Florida seasonal ingredients. In the same locally-inspired fashion, Market to Table also serves a modern American menu using southern ingredients, like Florida farm-raised chicken.

Grab a Round

For an after dinner aperitif, head to Pilar’s Martini in the Roper Garden Buildling for a cocktail and live music. The Roper Garden Building was built in 2008 as the first Certified Green Building in Winter Garden and features an aquaponic green house on the roof.

No visit to Winter Garden is complete without a stop at Crooked Can Brewing Company within the Plant Street Market . This craft brewery offers a variety of beers brewed on-site, from hoppy IPAs to smooth stouts—you can even take a tour of their facility. Pair your drink with a snack from one of the market’s food vendors specializing in snacks like gourmet mac n cheese, wood-fired pizza, or instagram-worthy acai bowls from Press’d Juice Bar .

Courtesy Oakland Manor House

Choose a Historic Stay

Take in the charm of this town with a stay at the historic 1926 Edgewater Hotel . The bed-and-breakfast maintains its historic ambience with tasteful period decor. Located right on Plant Street, it's the perfect base for exploring Winter Garden without needing to get in a car.

historicedgewater.com , 99 W Plant St, Winter Garden, FL 34787

Stay at a Charming Retreat

In the neighboring town of Oakland, you can get the same Old Florida experience staying in an authentic 1900s home at Oakland Manor House . The screened, wraparound porch is shaded in Spanish Moss and steps from Lake Apopka. 

oaklandmanorhouse.com , 620 N Tubb St, Oakland, FL 34760

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