Best Things to Do in Winter Park, FL (2026): 19 Local Picks

Looking for the best things to do in Winter Park? This walkable city mixes lakes, art museums and gardens within a few miles of Park Avenue. Take the Scenic Boat Tour through the chain of lakes, see the Tiffany chapel at the Morse Museum, and spend a Saturday morning at the farmers' market.

19 picks · Updated October 2026

1
Scenic Boat Tour

Tour in Park Avenue, $
The classic Winter Park outing: an hour on a pontoon through the chain of lakes and narrow cypress-lined canals. Tickets are $20 for adults and $10 for kids, sold first come, first served at the foot of Morse Boulevard.
- Outdoor
- Water
- Family
- Date idea
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2
Charles Hosmer Morse Museum of American Art

Museum in Park Avenue
Home to a remarkable Louis Comfort Tiffany collection, including a full chapel interior built for the 1893 Chicago world's fair. It sits right on Park Avenue.
- Indoor
- Rainy day
- Date idea
- Visitor favorite
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3
Winter Park Farmers' Market

Market in Park Avenue
Saturday mornings in Central Park's West Meadow bring produce, plants, baked goods and coffee. Pair it with a walk down Park Avenue or the boat tour.
- Outdoor
- Free
- Family
- Local favorite
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4
Albin Polasek Museum & Sculpture Gardens

Museum
The former home and studio of sculptor Albin Polasek on Lake Osceola, where you can tour the house galleries and walk lakeside gardens full of his work.
- Date idea
- Outdoor
- Indoor
- Local favorite
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5
Mead Botanical Garden

Park
Free, shaded trails, a boardwalk over wetlands, a butterfly garden and a pond full of turtles and wading birds. A quiet break that takes as long as you like.
- Free
- Outdoor
- Nature
- Family
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6
Rollins Museum of Art

Museum in Park Avenue
Rollins College's art museum (formerly the Cornell Fine Arts Museum) on the Winter Park campus, free to all visitors. It rotates exhibitions from its collection and also displays more than 100 works at The Alfond Inn nearby.
- Free
- Indoor
- Rainy day
- Date idea
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7
Kraft Azalea Garden

Park
A small lakeside garden on Lake Maitland where the Exedra monument, shaded by giant cypress, is a favorite place for sunset photos.
- Free
- Outdoor
- Nature
- Date idea
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8
Get Up and Go Kayaking - Winter Park

Outdoor activity
Clear-bottom kayaks let you see down into the lakes, and sunset or glow-in-the-dark night paddles turn a tour into a memorable evening.
- Outdoor
- Water
- Nature
- Date idea
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9
Hannibal Square Heritage Center

Museum in Hannibal Square
Cultural center run by Crealdé School of Art that documents the history of Hannibal Square, Winter Park's historic African American neighborhood. It hosts exhibitions, classes and community heritage events.
- Indoor
- Rainy day
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10
Winter Park Playhouse

Venue
A small professional theater on Orange Avenue focused on musicals, including the Florida Festival of New Musicals. Good for a night out after dinner nearby.
- Indoor
- Rainy day
- Date idea
- Local favorite
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11
Cady Way Trail

Park
About seven paved miles linking east Orlando, Baldwin Park and Winter Park, with water fountains and shaded rest stops. Leashed dogs are welcome.
- Free
- Outdoor
- Local favorite
- Dog friendly
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12
Winter Park History Museum

Museum in Park Avenue
Free museum just off Park Avenue covering Winter Park's past, from its citrus era onward, through rotating exhibits. A monthly family day adds kid-friendly tours and story time.
- Free
- Indoor
- Rainy day
- Family
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13
The Axe Trap

Entertainment spot
Axe throwing venue on Lee Road that pairs reservable lanes with a chef-run gastropub kitchen and a full cocktail bar. It also pulls espresso drinks and books parties and corporate outings.
- Indoor
- Rainy day
- Good for groups
- Date idea
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Aloma Bowl

Entertainment spot
Aloma Bowling Center on Aloma Avenue in Winter Park combines bowling lanes with an arcade, billiards and a bar and grill.

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15
Blue Bamboo Center for the Arts

Venue
Nonprofit performance space in Winter Park's Hannibal Square area with a busy calendar of jazz, swing, Latin and classical concerts. It also books comedy and tribute shows.
- Indoor
- Live music
- Date idea
- Local favorite
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16
Lake Baldwin Park

Park
Winter Park city park on Lake Baldwin where dogs can run off-leash throughout open hours, making it a favorite with dog owners. Shade trees, a sandy shoreline, a dock and picnic pavilions round it out.
- Walking
- Dog friendly
- Shaded
- Lake views
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17
Breakthrough Theatre

Venue
Small Winter Park theater company staging a full year of musicals, plays, Shakespeare and youth productions. It also offers homeschool classes, voice lessons and summer camps.
- Indoor
- Rainy day
- Date idea
- Family
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18
Howell Branch Preserve

Park
Small Winter Park nature preserve of about 10 acres ringed by wetlands, with a boardwalk and lookout deck for taking in the habitat. A fitness trail, playground and picnic pavilion make it an easy short outing.
- Walking
- Boardwalk
- Nature
- Wildlife
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19
Ward Park

Park
Large 66-acre Winter Park park packed with ballfields, tennis courts and an Olympic-size pool, plus an asphalt walking path and a trail that passes through wetlands.
- Walking
- Running
- Paved trail
- Restrooms
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How to plan a day in Winter Park

Start on Park Avenue, the city's main street, where the Morse Museum, the Winter Park History Museum and Central Park sit within a few blocks. On Saturday mornings, the farmers' market fills Central Park's West Meadow. Walk east on Morse Boulevard to the lake to catch the Scenic Boat Tour, which leaves hourly. Rollins College and its free art museum are at the south end of the avenue, and Hannibal Square lies just west.

In the afternoon, choose between gardens and the outdoors. The Polasek Museum sits on Lake Osceola, Kraft Azalea Garden is on Lake Maitland, and Mead Botanical Garden offers shaded trails and a boardwalk. For something active, ride the Cady Way Trail or book a clear-kayak tour. Evenings are good for the Winter Park Playhouse, The Axe Trap or Aloma Bowl.

Tips for visiting Winter Park

Park Avenue parking is tightest on weekends; side streets and public garages a block or two away are easier. The boat tour does not take reservations, so arrive early on weekends. In summer, plan outdoor activities for the morning and save museums for the hot, stormy afternoons.

About this list

Every place here is a locally run business in Orange County with its own website, which we checked for hours, menus and contact details. We leave national chains off our best-of lists and favor places with a clear specialty.

This page covers 19 things to do in Winter Park. You'll find them in Park Avenue and Hannibal Square.

What comes up again and again on their menus and websites: Rotating exhibitions.

About Winter Park

Winter Park sits just north of Orlando and is known for Park Avenue, Rollins College, its chain of lakes and brick streets. The city has a dense cluster of independent restaurants, boutiques, salons and professional offices.

Frequently asked questions

What is Winter Park best known for?

Winter Park is known for Park Avenue, its tree-lined shopping and dining street, and its chain of lakes connected by canals. The Scenic Boat Tour, the Morse Museum's Tiffany collection and Rollins College are among its best-known attractions. It sits just north of Orlando.

How much is the Winter Park Scenic Boat Tour?

Tickets are $20 for adults and $10 for kids. The narrated one-hour tour leaves hourly from the foot of Morse Boulevard and is first come, first served, so arrive early on weekends and holidays. Group rates are available for larger parties.

What can I do in Winter Park on a Saturday?

Start at the Winter Park Farmers' Market in Central Park's West Meadow, then walk Park Avenue and visit the Morse Museum. Take the Scenic Boat Tour in the afternoon, or walk the trails at Mead Botanical Garden. Finish with a show at the Winter Park Playhouse or a game at Aloma Bowl.