Outdoor Activities in Winter Park, FL (2026): 9 Local Picks

Looking for outdoor activities in Winter Park? The city's chain of lakes, shaded gardens and paved trails make it easy to spend a day outside. Tour the lakes by pontoon on the Scenic Boat Tour, paddle a clear kayak through the canals, or walk the boardwalk at Mead Botanical Garden.

9 picks · Updated October 2026

1
Scenic Boat Tour

Tour in Park Avenue, $
An hour on a narrated pontoon through Winter Park's lakes and cypress-lined canals, leaving hourly from the end of Morse Boulevard. Relaxed enough for any age.
- Outdoor
- Water
- Family
- Date idea
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2
Get Up and Go Kayaking - Winter Park

Outdoor activity
Guided clear-bottom kayak tours through the same Winter Park lakes and canals, including sunset and LED-lit night paddles. Private tours for up to ten people.
- Outdoor
- Water
- Nature
- Date idea
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3
Mead Botanical Garden

Park
Free shaded trails, a wetland boardwalk and a pond with turtles and wading birds, a cooler option when summer heat is high.
- Free
- Outdoor
- Nature
- Family
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4
Cady Way Trail

Park
About seven paved miles for biking, walking and skating, with water fountains, shaded rest stops and a playground. Leashed dogs are welcome, and it links to Baldwin Park.
- Free
- Outdoor
- Local favorite
- Dog friendly
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5
Kraft Azalea Garden

Park
Lakeside paths shaded by giant cypress lead to the Exedra monument on Lake Maitland, a favorite spot to watch the sun go down.
- Free
- Outdoor
- Nature
- Date idea
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6
Winter Park Farmers' Market

Market in Park Avenue
A Saturday morning in Central Park's West Meadow, browsing produce and plants under the oaks, is one of the easiest ways to enjoy Winter Park outdoors.
- Outdoor
- Free
- Family
- Local favorite
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7
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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8
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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9
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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Getting outside in Winter Park

Water is the main event. The Scenic Boat Tour leaves hourly from the foot of Morse Boulevard for an hour through the lakes and cypress-lined canals, no booking needed. For a hands-on version, Get Up and Go Kayaking runs guided clear-kayak tours on the same chain of lakes, including sunset and night paddles. On land, Mead Botanical Garden has wooded trails, a boardwalk and wildlife, and the Cady Way Trail suits a longer walk or ride.

Plan around the heat. From late fall to spring, any time of day works. In summer, go early in the morning or near sunset, bring water and sunscreen, and expect afternoon thunderstorms, which can pause boat and kayak tours. Kraft Azalea Garden on Lake Maitland is the best place to end the day.

Outdoor ideas for families and dog owners

Families should try Mead Botanical Garden, where kids can spot turtles and wading birds from the boardwalk, and the Scenic Boat Tour, which costs $10 for children. Leashed dogs are welcome on the Cady Way Trail, which also has a playground and picnic area. The Saturday farmers' market is an easy family morning followed by a walk along Park Avenue.

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 9 outdoor activities in Winter Park. You'll find them in Park Avenue.

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 outdoor activities are there in Winter Park?

Take the Scenic Boat Tour or a clear-kayak tour through the chain of lakes, walk the trails and boardwalk at Mead Botanical Garden, and ride or walk the paved Cady Way Trail. Kraft Azalea Garden on Lake Maitland is a favorite sunset spot, and the Saturday farmers' market fills Central Park.

Can you kayak in Winter Park?

Yes. Get Up and Go Kayaking runs guided clear-bottom kayak tours through Winter Park's chain of lakes and canals, including sunset tours and glow-in-the-dark night paddles. Private tours for up to 10 people can be arranged, which suits families and small groups.

Is the Cady Way Trail good for biking?

Yes. The Cady Way Trail is a paved multi-use path of about seven miles connecting east Orlando and Winter Park, with water fountains and sheltered rest stops. It connects to Baldwin Park and the Cady Way Pool, and leashed dogs are allowed.