Top 14 Activities in Winter Park, Florida

A cultural beacon for Greater Orlando, the picturesque city of Winter Park originated as a seasonal resort for affluent visitors in the 1880s.

Characterized by its canals, lakes, moss-adorned live oaks, and Mediterranean Revival architecture, I will never tire of discovering Winter Park.

This exploration can take place on foot, meandering beneath cypress trees at lakeside parks, or on the water where the Chain of Lakes is intertwined by winding canals.

The stylish downtown area, adjacent to Central Park, boasts an active station on the SunRail line. From this location, access to Orlando’s Central Business District can be achieved in just a few minutes.

This verdant hub serves as the backdrop for events such as one of Florida’s finest farmers’ markets and a nationally recognized art festival.

1. Charles Hosmer Morse Museum of American Art

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Located downtown, the Charles Hosmer Morse Museum of American Art houses one of the world’s most comprehensive collections of works by Louis Comfort Tiffany (1848-1944).

Displayed is an impressive selection of his leaded glass windows, jewelry, paintings, pottery, enamels, furniture, and lampshades.

Numerous items on display were salvaged from Tiffany’s residence and studio, Laurelton Hall, in Long Island after a fire in 1957.

Possibly my favorite exhibit is the complete interior of the chapel from the 1893 World’s Columbian Exposition in Chicago, which exudes opulence with its vibrant mosaics and windows in a Byzantine-Romanesque style.

2. Park Avenue

Flanked by Central Park, the east side features an inviting main street where, beneath the canopy of beautiful live oaks, a line of upscale independent businesses flourishes.

Along this brick-paved street, one can find boutiques and a diverse array of international restaurants, many of which feature outdoor seating under awnings and the oak canopy.

On Park Avenue and its adjoining streets, visitors can shop for luxurious home décor, jewelry, designer apparel, cosmetics, fashion accessories, fine art, and more.

The variety of cuisines is equally impressive, catering to every palette whether one craves smoothie bowls, New American fare, Turkish, Italian, French, Thai, Mexican, seafood, or steak.

This district is also framed by two prominent cultural landmarks in Winter Park: The Charles Hosmer Morse Museum of American Art to the north and Rollins College to the south, which counts Fred Rogers among its esteemed alumni and has welcomed presidents from Coolidge to Obama.

3. Central Park

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This verdant area serves as a complement to Park Avenue, hosting a variety of events and performances throughout the year. A recurring highlight is the Winter Park Farmers’ Market, which I will elaborate on later.

Additionally, Central Park presents a tranquil space for leisurely strolls or relaxation with a good book or companion. With its fountains, majestic old oak trees, and vibrant flowers, particularly in the rose garden during spring, it provides a beautiful escape.

Railroad tracks intersect the park from north to south, with Winter Park Station discreetly nestled within the greenery, serving Amtrak and SunRail commuter trains.

4. Albin Polasek Museum & Sculpture Gardens

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In 1950, Czech-American sculptor Albin Polasek (1879-1965) retired to Winter Park. Among his significant works are The Spirit of Music (1923) in Chicago’s Grant Park and The Yates Memorial in Springfield, Illinois (also 1923).

Overlooking Lake Osceola, Polasek’s purpose-built home and studio transformed into a museum in 1961.

This institution is unique in Florida, preserving much of its original furnishings, while the sculpture gardens offer sumptuous views over the water.

Approximately 200 works by Polasek are displayed, alongside pieces from his personal collection. For those seeking an educator’s insights into his life and contributions, a guided tour is highly recommended.

5. Rollins Museum of Art

Greater Orlando’s only teaching museum is situated on the campus of Rollins College. Established in 1978, the Rollins Museum of Art hosts a collection exceeding 5,000 works.

Its collection is diverse, emphasizing contemporary art, American painting up to 1950, and European Renaissance art.

During my visit, the museum was experiencing a notable expansion, featuring an engaging showcase of new acquisitions by artists such as John Singer Sargent, Benjamin West, and Thomas Cole.

Additionally, some of the museum’s collection is exhibited at the Alfond Inn, a refined boutique hotel whose proceeds contribute to scholarship funding.

6. Hannibal Square Heritage Center

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Beginning in the 1880s, the western section of Winter Park became the residence for the local African-American community. Early inhabitants engaged in railroad work or domestic service roles in affluent households.

In 2007, the Crealdé School of Art inaugurated a museum dedicated to documenting this important facet of Winter Park’s history.

The focus of the museum is the Heritage Collection: Photographs and Oral Histories of West Winter Park, a poignant exhibit comprising over 100 items that illuminate the African-American community’s heritage.

This collection is further complemented by a timeline outlining significant events from the Emancipation Proclamation to the election of Barack Obama in 2008.

7. Kraft Azalea Gardens

If you asked me how to conclude an idyllic day in Winter Park, I would recommend visiting this petite park at sunset. Spanning just five acres, Kraft Azalea Gardens is positioned on the southeast shore of Lake Maitland.

As the sun descends, the dense grove of cypress trees takes on an enchanting quality, making it no surprise that this park is a favored location for golden-hour photo sessions.

Visiting between late February and early June will likely grant you a view of the egrets that nest among these towering trees.

8. Mead Botanical Garden

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This remarkable botanical garden was inaugurated in 1940 as a tribute to the distinguished naturalist Theodore Luqueer Mead (1852-1936).

Initially, Mead’s acquaintances sought a location to house his extensive orchid collection. Over eight decades later, the Mead Botanical Garden serves as a delightful sanctuary tucked away within the city.

Winding paths and boardwalks guide visitors through wetlands and upland pine hammocks adorned with towering trees. The gardens feature a creek and a lively pond, home to wading birds and turtles.

A memorable highlight is the butterfly garden, showcasing a vibrant assortment of flowering plants that attract pollinators.

9. Casa Feliz Historic Home Museum

One notable figure instrumental in shaping Winter Park’s residential landscape was architect James Gamble Rogers II (1901-1990).

He is recognized primarily for the Florida State Supreme Court Building (1949) in Tallahassee; however, for much of the 20th century, he practiced in Winter Park, designing homes in various revivalist styles including Spanish Colonial and French Provincial.

An excellent representation of his early work can be found in the Robert Bruce Barbour House, constructed for a local industrialist in 1932. Known as Casa Feliz (Happy House), this residence features a rustic Andalusian style accentuated by a grand loggia.

During my tour, I appreciated several unique elements—such as the Spanish terracotta roof tiles, the majolica-tiled courtyards, and the impressive hand-hewn beams in the vaulted living room ceiling.

A well-presented museum exhibit chronicling James Gamble Rogers II’s contributions had recently opened during my visit.

10. Winter Park Farmers’ Market

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Hosted at Central Park West Meadow, the vibrant Winter Park Farmers’ Market ranks among Florida’s finest. The market operates on Saturdays from 8 AM to 1 PM, showcasing an abundance of local vendors in a compact space.

Along with seasonal produce, one may discover houseplants, herbs, sauces, wines, apple cider, maple syrup, seafood, pickles, cheeses, coffees, fresh breads, pet treats, and a multitude of artisanal crafts.

A valuable tip is to refrain from having breakfast beforehand, as there are numerous outstanding food trucks and vendors on-site. I have encountered Indian street food, arepas, chicken pot pies, acai bowls, breakfast burritos, ravioli, Belgian waffles, and BBQ options.

11. Scenic Boat Tours

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At the city’s lakeside parks, one will uncover a different side of Winter Park awaiting discovery.

Fringed with ferns, palms, oaks, cypresses, and stately mansions, the Chain of Lakes is connected by intricate canals. These sinuous waterways were originally constructed to transport lumber to a sawmill located on the shores of Lake Virginia at the chain’s southern end.

To truly appreciate Winter Park, it is essential to experience the lakes from the water. This can be achieved through scenic boat tours, departing daily on the hour from 10 AM to 4 PM.

These tours have been a tradition since the 1930s and open a gateway to a hidden world rich in biodiversity. The Chain of Lakes transforms into a wild habitat, home to alligators and an array of wading birds, yet remains opulent.

The grounds of Rollins College and numerous expansive estates surround the lakes and canals.

12. Winter Park Sidewalk Art Festival

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Attracting hundreds of thousands of visitors annually from across the nation, the Winter Park Sidewalk Art Festival stands out as a premier event.

Taking place in Central Park each March, this festival has become a tradition since 1960, ranking among the most esteemed art fairs in the country.

The event showcases a vast range of arts and crafts, encompassing paintings, jewelry, and contemporary mixed media.

Artists vie for accolades in over 60 categories, with prize totals exceeding $80,000, with the coveted Best of Show award rendering the festival particularly distinguished.

Throughout the three-day event, live music and entertainment are integral, beginning with a Friday night concert. Additionally, there is a children’s workshop and a complimentary bike corral available during the festival.

13. Winter Park Golf Course

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As is typical for Winter Park, the city’s nine-hole public golf course is nestled amid live oaks in a village-like setting.

The holes of Winter Park Golf Course are lined by two churches, majestic homes, a cemetery, and the passenger railroad tracks.

Established in 1914, the course underwent renovations in the 2010s and is recognized as one of the premier public short courses in the United States. I found this par-35 course to pose a significant challenge, particularly due to the small greens protected by sand traps.

The course features newly established fairways, greens, and roughs, complemented by a state-of-the-art irrigation system that has modernized the second-oldest course in Orlando for the 21st century.

14. Kayaking and Paddleboarding

If you wish to explore Winter Park’s Chain of Lakes more actively, several outfitters and tour companies are available.

Get Up and Go Kayaking, Otter Paddle Orlando, and Peace of Mind Kayak Tours all provide guided excursions in this stunning environment.

During these experiences, you will have greater freedom to observe wildlife or to linger in particularly scenic spots, whether that be a shaded oak-lined canal or a riverbank where you can see playful otters.

Sunset paddle tours are also available, and nighttime excursions featuring glow-in-the-dark elements can add a unique twist.

If you desire even more autonomy, Peace of Mind Kayak offers full or half-day rentals in Winter Park, complete with drop-off options.