Top Things to Do in Winter Park, FL in 2026

Looking for fun things to do in Winter Park, Florida? You’ve come to the right place. I live in Winter Park and love sharing my hometown.

Located just minutes north of downtown Orlando and only 20 minutes from the theme park madness (thanks to the I-4 Express Lanes), this charming city is definitely worth a detour.

Once a historic winter resort community, it has become an alluring destination with beautiful lakes, enchanting museums, pristine parks, great restaurants, and a walkable downtown. 

Whether you’re looking for outdoor adventures, cultural activities, or a relaxing getaway, Winter Park has something to offer every visitor.

Among its many offerings are world-class museums like the Albin Polasek Museum and Sculpture Gardens and the Charles Hosmer Morse Museum of American Art.

The Morse Museum houses an impressive collection of works from Louis Comfort Tiffany, plus other American Art Nouveau and Arts and Crafts pieces.

The Polasek Museum houses a unique collection of paintings, sculptures, drawings, and works on paper from renowned Czech-American artist Albin Polasek.

Winter Park also boasts some of Florida’s finest outdoor, natural attractions.

Take a leisurely stroll or bicycle ride around scenic Lake Virginia, or explore the lush natural beauty of Mead Botanical Garden.

History of Winter Park

Winter Park was called Lakeview until 1881 when two businessmen, Loring Chase and Oliver Chapman, decided they wanted the name to be more representative of a park in the winter … thus Winter Park was born.

To this day, the city still attracts many winter visitors because of its fantastic weather, relaxing lifestyle, and a plethora of great places to stay, shop and eat.

What makes Winter Park unique?

There are so many reasons to fall in love with this quaint city.

Winter Park’s vision statement sums up its essence: It is the city of arts and culture, cherishing its traditional scale and charm while building a healthy and sustainable future for all generations.

Winter Park’s downtown commercial district has interesting historic buildings and small businesses.

The city has several historic residential areas where it’s not uncommon to see peacocks roaming through the neighborhoods (Genius Drive).

There is a clear sense that this is a place where people live, work, go to school (Go Wildcats!) and play – it’s far from not a showpiece for tourists.

In 2015, Winter Park was featured in an award-winning Super Bowl commercial. Winter Park was the selected location because it symbolized the quintessential American hometown.

The city has also been featured in numerous articles, movies, and TV shows.

National Geographic Traveler magazine recognized the city as one of the world’s top historic destinations, noting, “This gracious town manages to retain its reputation as an oasis within the helter-skelter growth of Central Florida.”

Here are a few of my favorite hot spots in authentic Winter Park.

Winter Park Farmers’ Market

The Winter Park Farmers’ Market is held every Saturday morning from 8 am to 1 pm and is a great motivator to get out of bed.

Originally housed at an old train depot that is now a restored historical landmark on the corner of Morse Boulevard and S. New York Avenue, it has since moved to the space between the Winter Park train station and the Winter Park post office.

The current farmers’ market location provides more open space.

The market is a trendy community-gathering place that is a favorite for locals of all ages.

Since it’s in Winter Park, you can expect more upscale choices than at typical farmers’ markets.

The breakfast and lunch choices are stellar. Look for fresh crepes, arepas, pastries, and quiche. There’s always fresh-brewed coffee and healthy smoothies.

In fact, there is always a great selection of fruits, vegetables, and plants. And don’t miss the honey vendor.

Please note: The Winter Park Farmers’ Market closes each year on the third Saturday in March because of the Winter Park Sidewalk Art Festival. 

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Winter Park Historical Museum

The Winter Park Historical Museum is housed within the original train depot building. It’s open from 9 am until 1 pm on Saturday.

Admission is free, and exhibits put a historical focus on some of Winter Park’s traditions and events.

Winter Park Scenic Boat Tour

Established in 1938, the fleet of six 18-passenger boats travels through the pristine Winter Park Chain of Lakes on the Winter Park boat tour.

It is a definite MUST SEE for locals and visitors alike.

Every tour promises breathtaking views of nature and a historical overview of the luxurious private homes and estates along the shores.

Watch for the occasional water skier, yogi on a paddleboard, or sunbathing alligator.

The dock is less than a 5-minute walk from Park Avenue and is located on the East end of Morse Boulevard on Lake Osceola.

Admission is $20 for adults and $10 for children. Taxes are included (ages 2 through 11); those Under 2 are free.

They only accept cash or checks. Operating hours are 10 am to 4 pm daily (except Christmas). Boats leave on the hour.

Winter Park Boat Tour Address: 312 E Morse Blvd, Winter Park, FL 32789

Rollins College

Founded in 1885, Rollins College is Florida’s oldest recognized college and is consistently ranked by U.S. News and World Report as one of “America’s Best Colleges.”

The College of Arts and Sciences offers full-time undergraduate programs in the liberal arts.

The Crummer Graduate School of Business is consistently ranked by Forbes magazine among the best business schools for return on investment.

Forbes has ranked the MBA program No.1 overall in Florida.

The Hamilton Holt School serves the Central Florida community by offering exceptional undergraduate and graduate degree programs.

The classes occur during evenings and weekends for students diverse in age, experience, and professional development.

The Rollins 70-acre campus contains a range of amenities, including a theater for performing arts, the Cornell Campus Center, and the Alfond Sports Center.

Rollins also owns and operates a full-service hotel nearby called the Alfond Inn. We recommend this to anyone needing overnight accommodations.

Located on the banks of lovely Lake Virginia, it’s a great campus to walk around informally.

Contact the Office of Admission or visit this link to set up a campus tour.

While there, be sure to take the Mister Rogers Walking Tour. Fred Rogers is one of several celebrities who graduated from Rollins.

Rollins College Address: 1000 Holt Ave, Winter Park, FL 32789

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The Charles Hosmer Morse Museum of American Art

Opened in 1995, The Charles Hosmer Morse Museum of American Art (“The Morse Museum”) houses the most comprehensive collection of works by American designer Louis Comfort Tiffany (1848–1933).

The chapel interior he designed for the 1893 World’s Columbian Exposition in Chicago and art and architectural elements from his Long Island estate, Laurelton Hall.

Highlights also the restored Daffodil Terrace, prize-winning leaded-glass windows, iconic Tiffany lamps, and custom furnishings among the featured installations.

Visitors will also enjoy the exhibits of American art pottery, Arts and Crafts furnishings, and late 19th- and early 20th-century American painting and graphics.

The Morse Museum is open from 9:30 am – 4 pm Tuesday through Saturday and Sunday from 1 pm – 4 pm. Closed Monday and most major holidays.

Admission is $6 for adults, $5 for seniors 60 and older, and $1 for students (with valid ID). The museum is free for children younger than 12.

The Morse Museum Address: 445 North Park Avenue, Winter Park, FL 32789

Albin Polasek Museum and Sculpture Gardens

The Albin Polasek Museum and Sculpture Garden (“The Polasek”) in Winter Park promotes the legacy of internationally known Czech-American sculptor Albin Polasek.

It also enriches lives through the power of inspiration conveyed by his story, setting, and art.

The Polasek features over 200 works by Albin Polasek.

In 2000, Albin Polasek was named a “Great Floridian” by the state of Florida, a distinction that recognizes those who made significant contributions to the history and culture of the state.

In 2004, the Florida Artists Hall of Fame inducted Albin Polasek.

The Polasek is also on the National Register of Historic Places and National Trust of Historic Artists Homes/Studios.

The Polasek hosts events like the “Winter Park Paint Out” and is available for weddings and meeting rentals.

The Albin Polasek Museum and Sculpture Gardens is a 501(C)(3) public charity, a non-profit organization whose budget is also funded by donations and membership.

All donations and dues support its preservation, maintenance, and operation.

The Polasek is open Tuesday through Saturday from 10 am – 4 pm; Sunday from 1 pm – 4 pm. Admission is $12 for adults, $10 for Seniors (60+) and College Students, $7 for Students (K-12). Members and children under 4 are free.

Free Days include Heritage Day and also Veterans Day.

The Albin Polasek Museum and Sculpture Gardens Address: 633 Osceola Ave, Winter Park, FL 32789

Casa Feliz Historic Home

“Happy House”, also known as Casa Feliz, is the beautifully restored Spanish Farmhouse designed by acclaimed architect James Gamble Rogers II.

The exterior of the house and grounds are picture-perfect and an amazing place for weddings and other special events.

The rich textures of original Spanish roof tiles and whitewashed century include old bricks, a turret, a bell tower, a heavy timber balcony detailed in colors of the Mediterranean, and lush landscaping.

There are also incredible courtyards, sweeping oaks, and native plants – making it a must-see in Winter Park.

Casa Feliz is open to the public free of charge for self-guided tours on Tuesday and Thursday from 10 am – 12 pm.

“Music at the Casa” also happens on Sundays from 12 pm – 3 pm. Private tours are arranged by calling 407.628.8200.

Casa Feliz hosts special events for the public throughout the year and especially around the holidays.

FYI: Santa Claus also always makes a pit stop at Casa Feliz.

Casa Feliz Address: 656 N Park Ave, Winter Park, FL 32789

Park Avenue Shopping District

One of the best ways to describe Park Avenue is that new-world sophistication meets old-world charm.

Park Avenue borders the crown jewel of all the city’s parks. This 11-acre park boasts shady oak trees, landscaped planters, sitting areas, open space, and three beautiful fountains.

It’s home to one of the most famous art festivals in the country each Spring, The Winter Park Sidewalk Art Festival.

There is even a rose garden at Central Park’s southern corner where you can stop and smell the roses. The lush foliage and relaxing atmosphere make it the perfect spot for a picnic.

In addition to the art festival, Winter Park hosts a variety of outdoor concerts and movie screenings throughout the year.

Park Avenue is home to an array of unique boutiques and gift shops, world-renowned art museums, chic salons/spas, and epicurean delights from sidewalk cafes and trendy wine rooms to fine dining and gastro pubs

Often called “Little Europe,” Park Avenue is a destination that has provided the citizens and visitors of Winter Park with an elegant place to stroll, dine, and shop for many decades.

Authentic Florida Trivia Question:

Where was the world-famous “temple” orange discovered? (FYI: The Temple is technically a hybrid known as a “tangor”, a cross between a tangerine and an orange.)

Answer: Winter Park

More recommendations from our readers and Authentic Florida Facebook Followers:

• Winter Park Library: 1052 W Morse Blvd, Winter Park, FL 32789
• Center for Health and Wellbeing: 2005 Mizell Ave #800, Winter Park, FL 32792
• Hannibal Square: 642 W New England Ave, Winter Park, FL 32789
• Sit at the lake on Hillstone: 215 S Orlando Ave, Winter Park, FL 32789
• Aloma Cinema Grill: 2155 Aloma Ave, Winter Park, FL 32792
• Winter Park Playhouse: 711 N Orange Ave, Winter Park, FL 32789
• Kraft Azalea Gardens: 1365 Alabama Dr, Winter Park, FL 32789
• Mead Gardens: 1300 S Denning Dr, Winter Park, FL 32789

If you enjoyed this article on things to do in Winter Park, check out these other areas not far away:

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• Celebrating the Historic Town of Eatonville, Florida
• Best Things to Do in Altamonte Springs
• 7 Ways to Experience Orlando Like a Local
• Our Favorite Things to Do in Sanford
• Best Things to Do in College Park Orlando
• Best Things to Do in SoDo Orlando

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