25 Things to Do in Winter Park
Park Avenue and the surrounding Winter Park community offer residents and visitors a variety of activities. From enjoying one of our local parks and exploring a museum, to dining al fresco and attempting to paddle board, the Winter Park, Florida area is rich in exceptional experiences.
1. Park Avenue Shopping District
The centerpiece of a lavish winter retreat since 1887, Park Avenue, Winter Park 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. 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 is a year-round destination that is sure to charm visitors of all ages. For more information on shopping and dining on Park Avenue, click here.
2. The 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, as well as 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 tours 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, FL chain. Every tour guarantees plenty of swaying palms, towering cypress trees, lush ferns, and a variety of flourishing subtropical 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. Tours are available for individuals, groups, and private events throughout the year. To learn more about the Winter Park Scenic Boat Tour, click here.
5. Dining on Park Avenue
Park Avenue Winter Park’s eateries offer something to suit every taste, especially foodies! This culinary utopia is home to over 40 Winter Park restaurants, including everything from ice cream 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 Winter Park District, or a special dinner with family and friends, Winter Park 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 wine bar. For more information and to view a listing of Park Avenue dining options, click here.
6. Central Park
Central Park Winter 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, Winter on the Avenue, the annual Pancake Breakfast before the Christmas Parade, and the Olde Fashioned 4th of July Celebration. Enjoy this oasis of nature in the heart of Winter Park, Florida. To learn more information about Central Park, click here.
7. Winter Park Farmers’ Market
The Winter Park Farmers’ Market is now held every Saturday morning at the West Meadow at the corner of New York and Morse Avenues. 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 Winter Park, FL, 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 College was named one of the 50 Most Amazing College Campuses in 2011 by The Best Colleges, and the number one private regional university in the South and number two among all 133 universities in the South in 2025 by U.S. News & World Report. Feel free to stroll 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. You'll also find a bronze statue of legendary television host Mr. Fred Rogers, one of Rollins' most famous graduates. Take a relaxing walk on the lakeside walking trail, visit the Rollins Museum of Art, 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 Winter Park, click here.
9. Rollins Museum of Art
Set like a jewel on the Rollins College campus overlooking beautiful Lake Virginia, the Rollins Museum of Art 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, drawings, 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, a 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 add to the historic beauty of the restored farmhouse. The lush landscaping—courtyards, sweeping oaks, and native plants contained by ancient clay amphorae—adds to the historic beauty of the restored farmhouse. Casa Feliz Winter Park offers tours on Tuesday and Thursday from 10 a.m. – 2 p.m. and an open house on Sunday from noon – 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 Winter Park including upcoming events, click here.
11. Winter Park History Museum
Explore the fascinating history of Winter Park at the Winter Park History Museum. The museum collects, preserves, and shares the history of Winter Park, FL and the surrounding areas. It hosts various educational programs and curates exhibits on Winter Park, FL 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.
12. The Bach Festival Society of Winter Park
The Bach Festival Society of Winter Park holds the distinction of being the third-oldest continuously operating Bach Festival in the United States, as well as Central Florida’s oldest performing arts organization. With over 160 singers, many of whom are local music educators, the choir shares a love for great music and often collaborates with renowned musicians. The Bach Festival Society attracts world-class talent, contributing to the Winter Park cultural scene. To learn more about upcoming performances, click here.
13. Popcorn Flicks in the Park
The City of Winter Park and Enzian Theater collaborate to produce “Popcorn Flicks” cinema series in Winter Park. These outdoor movie nights are a local favorite, typically held on the second Thursday of each month at 8 p.m. Popcorn Flicks take place in Central Park Winter Park and are free to the public, offering a great way to experience downtown Winter Park while enjoying classic films. Bring a blanket, relax, and enjoy a wonderful community experience. To learn more about Popcorn Flicks, click here.
14. Mead Botanical Garden
Described as “an urban oasis,” Mead Botanical Garden is a haven for wildlife and nature lovers, located just a few miles from Winter Park, Florida’s downtown district. The garden emphasizes sustainability, environmental learning, and provides a serene space for contemplation, recreation, and celebration. The garden is also a perfect venue for intimate gatherings or group events. If you're in the area, check out the various programs and events hosted throughout the year. For more information, click here.
15. Kraft Azalea Garden
Kraft Azalea Garden, an 11-acre park near Winter Park, FL, offers peaceful waterfront views and is perfect for those looking for a tranquil retreat. The garden, located on Lake Maitland, features benches for reading, picnicking, and beautiful walking trails. It's especially lovely from January through March when the azaleas bloom. Don’t forget to take a relaxing walk along the shores of Lake Maitland and enjoy nature’s beauty. For more information, click here.
16. Winter Park Golf Course
Winter Park Golf Course, established in 1914, is one of the oldest golf courses in Central Florida. It stretches through downtown Winter Park and offers a challenging course for both seasoned and amateur golfers. The golf course provides an opportunity to enjoy the area’s natural beauty, and is close to the heart of Winter Park’s historic district. To book your tee time or learn more, call 407-599-3419 or click here.
17. The Alfond Inn
The Alfond Inn in Winter Park plays a significant role in enhancing the city’s cultural reputation by housing over 240 works of contemporary art. The inn’s collection, an extension of the Rollins Museum of Art, offers public access to a rich variety of paintings, sculptures, and mixed-media works. Be sure to experience an art tour at the inn and indulge in the dining options at Hamilton’s Kitchen. To make a reservation or learn more, click here.
18. Hannibal Square
The historic Hannibal Square neighborhood, located just blocks from Park Avenue Winter Park, offers unique boutiques, al fresco dining, Shady Park, and a variety of local businesses. Enjoy exploring the charming area, filled with exciting boutiques, or enjoy a meal at one of the local restaurants. To discover more about Hannibal Square, click here.
19. Cultural Walking Tour
Take a self-guided walking tour of Winter Park, highlighting its historical treasures, museums, and landmarks. The tour starts near the Winter Park Golf Course and heads south along Park Avenue, showcasing museums like the Charles Hosmer Morse Museum of American Art and architectural gems like Casa Feliz. A visit to Rollins College is also part of the route, where you can enjoy beautiful views of the lakes and impressive historical sites. Download the guide for more details here.
20. 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, FL to Orlando was 15 cents, and the trip measured six miles and took half an hour. The depot was removed in 1967. But look for a monument, a little to the west of Dinky Dock on Lake Virginia, that marks 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.
21. Winter Park Library
The new Winter Park Library, designed by world-renowned artist and architect Sir David Adjaye, opened in 2021 next to Martin Luther King Jr. Park in Winter Park, FL. This new landmark offers a variety of amenities to residents and visitors in the City of Winter Park, including a studio for audio and video production, a library commons, private study rooms, a computer lab, a 3D printer, arts and crafts room, bikes you can check out, and much more. A collection of over 280,000 books, audiobooks, music cassettes and CDs, videos, DVDs, and eBooks are available, including 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 story times and special events for kids of all ages.
Winter Park Chamber of Commerce President and CEO Betsy Gardner Eckbert interviewed Sir Adjaye. To watch this interview, click here. The library is open to the public Monday to Saturday and closed on Sundays. For more information about Winter Park Library, click here.
22. Winter Park Playhouse
The Winter Park Playhouse is the only professional musical theater in Central Florida dedicated to showcasing Broadway-quality performances. Located just blocks from Park Avenue, the playhouse offers year-round productions of musical comedies, revues, and cabarets. It’s a must-visit destination for theater lovers in Winter Park. To learn more about current performances or to buy tickets, click here.
23. Winter Park Village
The Winter Park Village is a pedestrian-focused shopping and dining district between 17-92 and Denning Drive. Shops and restaurants abound, along with spas, The Bar Method fitness studio and a movie theater. There is frequent live entertainment and several outdoor gathering areas to relax and enjoy the Florida weather. Click here to learn more.
24. Central Florida Community Arts
After years of music-making, the founders of Central Florida Community Arts, Joshua Vickery and Jonathan Cole, came to the realization that Central Florida does not offer many cultural platforms for ALL musicians to use their talents. Therefore, in September of 2010, they decided to begin the journey of creating an incredible community arts program in Winter Park, FL. They began reaching out to influential people in the Central Florida area, and every one of them responded with overwhelming support – thus, Central Florida Community Arts was born. Since then, many people have been working hard to make this dream become a reality in the City of Winter Park.
After a successful kickoff in February 2011, CFCArts performed their inaugural concert to over 1,200 people in May of 2011, with a choir of over 130 singers and an orchestra of over 35 players. That community choir has since grown into several separately-themed choirs with over 500 members total, and their per-concert audience has grown to upwards of 5,000 patrons. For those looking to experience the arts in Winter Park, FL, these performances are a great opportunity to engage with the local community.
To learn more about upcoming performances and events in Winter Park, click here.
25. Special Events
Winter Park, FL hosts a variety of special events throughout the year, ensuring there is always something exciting happening. From the Winter Park Art Festival to the annual Christmas Parade, there's no shortage of fun, festive activities. Experience Winter Park’s Park Avenue during the holidays with events like Winter on the Avenue, or visit Central Park Winter Park for seasonal celebrations. Don't miss out on the fun – learn more about upcoming events here.
Parking
Self-Parking Options (see parking map):
On-street parking is available for up to 3 hours.
Free 4-hour parking is available in municipal parking lots within one block of Park Avenue Winter Park.
North Park Avenue garage offers complimentary parking on the 4th & 5th floors only (4-hour parking).
South Park Avenue garage (Truist Parking Garage) offers paid parking by the hour.
Valet Parking Options: Complimentary valet available at New England & Park avenues. Additional valet locations available across from Cocina 214 (along Welbourne Avenue) and at Prato (North Park Avenue).