15 Best Things to Do in Winter Park, FL

By VI Staff on July 3, 2020 - Updated

City of Winter Park - Government

Five miles north of downtown Orlando in central Florida’s Orange County, Winter Park is a leafy city with plenty of wide-open spaces, green urban parks, pristine golf courses, and balmy, year-round weather that is a popular spot for outdoor recreation. The quaint cobbled streets of the historic downtown area are lined with beautiful European-style buildings and the city is home to interesting museums like the Charles Hosmer Morse Museum of American Art. Explore antiquities and contemporary works at the Cornell Fine Arts Museum on the shores of Lake Virginia, or enjoy an array of outdoor activities like hiking, water-based sports on the lake, or a game of golf on one of the many world-class golf courses. CDC information for travelers. Hours/availability may have changed.

1.Charles Hosmer Morse Museum of American Art

Located on North Park Avenue, the Charles Hosmer Morse Museum of American Art is a world-renowned museum with an unrivaled collection of art nouveau, including the world’s greatest collection of the works by American artist and designer Louis Comfort Tiffany (1848–1933). The museum exhibits collections of Tiffany’s famed leaded-glass lamps and windows, as well as pottery, paintings, jewelry, and art glass, and a magnificently restored Byzantine-Romanesque chapel interior. The museum also features exhibits of American paintings from the late 19th- and early 20th-century, the Arts and Crafts movement, and American art pottery.

445 N Park Ave, Winter Park, FL 32789, Phone: 407-645-5311

2.Albin Polasek Museum & Sculpture Gardens

Located on three acres on Osceola Avenue with lovely views over Lake Osceola, the Albin Polasek Museum and Sculpture Gardens is dedicated to showcasing the works of the famous Czech sculptor, Albin Polasek who spent many years of his life in Florida. Founded in 1961, the museum is based in the building that was once his home and studio for more than 50 years and features a fine art collection of American representational sculpture with over 200 works on display. Visitors can enjoy guided tours of the historic residence and adjacent chapel to get an insight into the sculptor’s life, as well as the beautiful outdoor sculpture garden. The Albin Polasek Museum and Sculpture Gardens host several cultural events throughout the year, including a Chamber Concert Series and the Winter Park Paint Out.

633 Osceola Ave, Winter Park, FL 32789, Phone: 407-647-6294

3.Kraft Azalea Gardens

Located on the shore of Lake Maitland, the Kraft Azalea Garden is a scenic public park shaded by enormous cypress trees with peaceful grassy picnic spots, cobblestone paths, walking paths, and benches for reading and relaxing. Established by George and Maud Kraft in 1938, the Kraft Azalea Garden has a tranquil and romantic atmosphere with cypress canopies, a picturesque Greek exedra monument with a semicircle of white colonnades, and a small dock for fishing on the lake. The park is said to be the home of the northern-most banyan tree in the state and boasts a bright and colorful display of blooming flowers from January through March.

1365 Alabama Dr, Winter Park, FL 32789, Phone: 407-599-3334

4.Rollins College

Rollins College is a private liberal arts college that offers several graduate programs and boasts one of the most beautiful campuses in the country. Founded in 1885, the college is a four-year, co-educational institution with 60 undergraduate and graduate majors and minors, including unique courses such as Strategies for Changemakers, Job Market Boot Camp, and The Science of Sustenance. The college hosts Fox Day every spring when classes are canceled by the president due to the beautiful weather and students can head to the on-campus swimming pool or one of the many nearby lakes to kick back and relax.

1000 Holt Ave, Winter Park, FL 32789, Phone: 407-646-2000

5.Mead Botanical Garden

Located on South Deming Drive, Mead Botanical Garden is an immense, tranquil green space and urban oasis that is home to a plethora of fauna and flora from all over the globe. Just a few miles from the downtown business district, the garden offers a peaceful escape from the hustle and bustle of the city, where visitors can enjoy the wide variety of trees, flowering gardens, freshwater ponds, and wildlife habitats. The gardens are crisscrossed with walking paths and secluded picnic spots and have several pavilions that can be used for private functions and events.

1300 S Denning Dr, Winter Park, FL 32789, Phone: 407-622-6323

6.Casa Feliz Historic Home Museum

The Casa Feliz Historic Home Museum, also known as the Robert Bruce Barbour House, is a beautifully restored Spanish farmhouse overlooking the golf course in the heart of Winter Park. Designed by renowned architect James Gamble Rogers II, the house is one of his best-known residences and features beautiful architectural elements such as whitewashed century-old bricks, Spanish roof tiles, a turret, and bell tower, and a wide timber balcony in warm, Mediterranean hues. Interiors have vaulted ceilings, arched doorways, a spiral staircase, and a Majolica-tiled interior courtyard and fountain and hand-carved European antiques in every room. The house is surrounded by lush gardens and landscapes, creating a beautiful backdrop for special occasions like weddings.

656 N Park Ave, Winter Park, FL 32789, Phone: 407-628-8200

7.Cornell Fine Arts Museum

Based on the campus of the Rollins College overlooking the tranquil waters of Lake Virginia, the Cornell Fine Arts Museum is home to a diverse collection of more than 5,000 works of art and is considered one of the nation’s most innovative college art museums. The museum’s comprehensive collection features objects that span centuries from ancient art and artifacts and hosts an array of rotating exhibitions, ongoing programs, and other art-related events. The museum has an education gallery for younger visitors that features hands-on activities to encourage creativity and cognitive skills and a museum shop that sells art books and museum-published titles.

1000 Holt Ave, Winter Park, FL 32789, Phone: 407-646-2526

8.Cady Way Trail

The Cady Way Trail is a 6.5-mile multiuse rail trail that is popular for hiking, jogging, mountain biking, and other recreational activities. The trail was created along the abandoned roadbed of the East Florida & Atlantic Railroad and traverses Baldwin Park that extends from the Fashion Square Mall in Orlando to Cady Way Park. The trail passes a pastoral golf course and the spectacular homes of Winter Park and joins a network of existing walking, hiking, and biking trails in the area. Parts of the trail feature architectural elements reminiscent of pre-1940s Central Florida, as well as an oak-tree canopy that provides welcome shade on certain portions of the trail.

Cady Way Trail, Winter Park, FL 32792

9.Winter Park Distilling Company

The Winter Park Distilling Company is a locally owned distillery that began as a small, home-based business and has grown into the finest craft distillery in Orange County. Founded in 2010 by Paul Twyford and Andrew Asher, Winter Park Distilling Company produces a range of high-quality, handcrafted spirits such as bourbon, rum, vodka, and whiskey. The award-winning distillery has an online shop that sells spirits and Winter Park Distilling Company merchandise and offers guided distillery tours and tastings throughout the week.

1288 N Orange Ave, Winter Park, FL 32789, Phone: 407-801-2714

10.Hannibal Square Heritage Center

The Hannibal Square Heritage Center is a community center run by the Crealdé School of Art that focuses on arts, crafts, and culture produced by Winter Park's African-American community. Located on New England Avenue in the historic neighborhood of Hannibal Square, the center hosts permanent and traveling exhibits of artworks, and a variety of educational programs, workshops, and symposiums that highlight the past, present, and future contributions of local African-American artists. The 3,000square-foot Heritage Center can be rented for private and special events.

642 W New England Ave, Winter Park, FL 32789, Phone: 407-539-2680

11.Crealde School of Art

The Crealdé School of Art is a non-profit arts organization that offers visual and three-dimensional art classes for all ages. Located on St Andrews Boulevard, the school was opened in 1975 and has been offering art-related classes, workshops, summer art camps, and visiting artist workshop series to the community ever since. The school features two large exhibition galleries showcasing works by local, national, and international artists, and the school's students, and an outdoor sculpture garden that offers a peaceful escape from the city. The Crealdé School of Art also runs the Hannibal Square Heritage Center on New England Avenue in the historic neighborhood of Hannibal Square.

600 St Andrews Blvd, Winter Park, FL 32792, Phone: 407-671-1886

12.Winter Park Public Library

The Winter Park Public Library is an education-focused institution with a 33,000 square-foot facility on New England Avenue that offers a wide range of services. The library houses a collection of over 280,000 items, including the latest large-print books, fiction, and non-fiction books, audiobooks, eBooks, and audio-visual titles. The Children’s Library is packed with all kinds of materials for children of all ages, including books, audiotapes, videos, and DVDs, and hosts storytimes and special events for younger library users. The library is open to the public daily and offers services such as access to the Internet, word-processing, printing, and research.

460 E New England Ave, Winter Park, FL 32789, Phone: 407-623-3300

13.Ethos Vegan Kitchen

Ethos Vegan Kitchen is a laid-back vegan restaurant and bar in a spacious, loft-like space at the foot of Antique Row on Orange Avenue. The restaurant has exposed brick walls, wooden beams, comfortable décor, and a cozy outdoor courtyard and serves a meat-free menu of delicious, made-from-scratch vegan and vegetarian fare. Dishes like pecan-encrusted eggplant, meat-free shepherd's pie, pizza with broccoli and banana peppers, and a variety of gourmet sandwiches and homemade soups are made with locally sourced, organic, and chemical-free ingredients. The cuisine is accompanied by a wide range of craft brews and a curated selection of New World wines.

601-B S New York Ave, Winter Park, FL 32789, Phone: 407-228-3899

14.Bulla Gastrobar

Bulla Gastrobar is a casual, contemporary bar that serves authentic Spanish and Catalan tapas and small sharing plates, and made-to-order sangria in a laid-back setting with a convivial Mediterranean vibe. The menu features a mouth-watering array of traditional tapas like patatas bravas, grilled polpi (octopus), fried calamari, and tuna tartar, as well as entrées like fresh seafood, prime steaks, steaming paellas, and Spanish-influenced pub burgers. An open-air patio is ideal for sipping homemade sangria or a gentle Rioja and watching the world go by.

110 S Orlando Ave #7, Winter Park, FL 32789, Phone: 321-214-6120

15.Hunger Street Tacos

Hunger Street Tacos is a popular counter-serve spot that offers authentic Mexican street fare like tacos, quesadillas, burritos, and enchiladas in a vibrant setting. Based in a building boasting artful murals by local artists on Fairbanks Avenue, the café serves all the regular favorites like tacos stuffed with seared brisket, chorizo, and scrambled egg, and signature bites like squash blossom quesadillas. Walls are adorned with artworks and murals by the Lapiztola Collective, which was founded by designers Roberto Vega and Rosario Mtz, and architect Yankle Balderas, and local artist Liseth Amaya. The café has a lovely covered patio with seating for outdoor dining.

2103 W Fairbanks Ave, Winter Park, FL 32789, Phone: 321-444-6270