Best Walking Trails in Winter Park, FL (2026): 6 Local Picks

Looking for the best walking trails near you in Winter Park? Here are 6 walking trails worth the trip, starting with Cady Way Trail and Mead Botanical Garden, with what each one does best and how to get there.

6 picks · Updated October 2026

1
Cady Way Trail

Park
A paved trail of about 7.2 miles between east Orlando and Winter Park, with water fountains and sheltered rest stops. It is stroller-friendly and connects to Baldwin Park.
- Walking
- Free
- Outdoor
- Local favorite
Call Cady Way Trail Website for Cady Way Trail (opens in a new tab)Directions to Cady Way Trail (opens maps)
2
Mead Botanical Garden

Park
A free natural garden with shaded wooded trails, a boardwalk over wetlands and a pond that draws wading birds and turtles. It is one of the best short nature walks close to town.
- Walking
- Free
- Outdoor
- Nature
Call Mead Botanical Garden Website for Mead Botanical Garden (opens in a new tab)Directions to Mead Botanical Garden (opens maps)
3
Kraft Azalea Garden

Park
A small, free lakeside garden on Lake Maitland with cypress-shaded paths and the Exedra monument, a favorite spot for sunset photos.
- Walking
- Free
- Outdoor
- Nature
Call Kraft Azalea Garden Website for Kraft Azalea Garden (opens in a new tab)Directions to Kraft Azalea Garden (opens maps)
4
Lake Baldwin Park

Park
A shady 23-acre park on Lake Baldwin where dogs can run off-leash during open hours, with a sandy shoreline, dock and restrooms.
- Walking
- Dog friendly
- Shaded
- Lake views
Call Lake Baldwin Park Website for Lake Baldwin Park (opens in a new tab)Directions to Lake Baldwin Park (opens maps)
5
Howell Branch Preserve

Park
A small Winter Park preserve with a wheelchair-accessible boardwalk and lookout deck over wetlands, plus a fitness trail. Parking at the entrance is limited.
- Walking
- Boardwalk
- Nature
- Wildlife
Call Howell Branch Preserve Website for Howell Branch Preserve (opens in a new tab)Directions to Howell Branch Preserve (opens maps)
6
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
Call Ward Park Website for Ward Park (opens in a new tab)Directions to Ward Park (opens maps)

Choosing a walking trail in Orlando

Decide first how far you want to go. For long, flat walks, the paved rail-trails and greenways are best: the West Orange Trail, the Cady Way Trail and the Little Econ Greenway all let you walk out and back as far as you like. For a loop, Lake Eola is just under a mile and Lake Underhill is about 1.3 miles. If you want shade and scenery over distance, Mead Botanical Garden, Leu Gardens and Kraft Azalea Garden are short and pretty. Boardwalk fans should try Mead Garden, Howell Branch Preserve or Lake Fairview Park.

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 6 walking trails in Winter Park.

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

Where can I walk a paved trail in Winter Park?

The West Orange Trail, Cady Way Trail and Little Econ Greenway are the longest paved options, at roughly 22, 7.2 and 7.4 miles. For shorter paved loops, try the 0.9-mile path around Lake Eola or the 1.3-mile Lake Underhill Path.

What is the best walking trail in Winter Park?

The West Orange Trail is the longest and most popular, with about 22 paved miles through Winter Garden. Closer to downtown, the Lake Eola loop and the Cady Way Trail are local favorites, and Mead Botanical Garden is the pick for a shaded nature walk with a boardwalk.

How long is the walk around Lake Eola?

The paved path around Lake Eola is about 0.9 miles. The park is open daily from 6am to 11:59pm, and you can stop at the fountain, playgrounds or swan boat rentals along the way.

Are there boardwalk trails in Winter Park?

Yes. Mead Botanical Garden in Winter Park has a boardwalk over wetlands, Howell Branch Preserve has a boardwalk and lookout deck, and Lake Fairview Park has a boardwalk with an observation deck by the boat ramp.

Where can I walk in nature near downtown Winter Park?

Mead Botanical Garden and Kraft Azalea Garden in Winter Park are short drives from downtown, and Harry P. Leu Gardens is in the Audubon Park area. Dickson Azalea Park is a small, shaded city park close to downtown.