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Walking trails near Winter Park, FL

197 walking trails within 30 miles of Winter Park. Tap a trail for its map, trailhead and directions.

0.4 mi long · Easy · Winter Park

Hiking Biking Paved

2.5 mi long · Easy · Orlando Families, Parks and Recreation

Hiking Biking Paved

491

1.7 mi away

2.5 mi long · Easy · Azalea Park

Hiking Biking Paved

0.6 mi long · Easy · Union Park

Hiking Biking Paved Greenway

75

2.3 mi away

1.8 mi long · Easy · Union Park

Hiking Biking Paved

Cady Way Trail

2.4 mi away

0.6 mi long · Easy · Union Park

Hiking Paved

Cady Way Trail

3.0 mi away

1.4 mi long · Easy · Orange County Parks and Recreation

Hiking Biking Paved

0.6 mi long · Easy · Orlando

Hiking Biking Paved

Alden Road Trail

3.0 mi away

0.3 mi long · Fairview Shores

Hiking Biking Mountain biking

Cady Way Trail

3.0 mi away

0.7 mi long · Easy · Azalea Park

Hiking Paved

Cady Way Trail

3.0 mi away

5.8 mi long · Easy · Orange County Parks and Recreation

Hiking Biking Paved

493

3.1 mi away

1.2 mi long · Easy · Azalea Park

Hiking Biking Paved

0.7 mi long · Easy · Orlando

Hiking Biking Paved

Wirz Trail

3.4 mi away

4.1 mi long · Easy · Casselberry Parks and Facilities

Hiking Biking Paved

7.2 mi long · Easy · Orange County Parks and Recreation

Hiking Biking Paved Greenway

3.0 mi long · Easy · Orlando Families, Parks and Recreation

Hiking Biking Paved

2.6 mi long · Easy · Orlando Families, Parks and Recreation

Hiking Biking Paved

Kewannee Trail

3.7 mi away

1.6 mi long · Seminole County Parks and Recreation

Hiking Biking Mountain biking

Wirz Trail

4.0 mi away

1.1 mi long · Easy · Casselberry Parks and Facilities

Hiking Biking Paved

0.9 mi long · Easy · Orlando

Hiking Biking Paved

2.0 mi long · Easy · Union Park

Hiking Biking Paved Greenway

Bikeway 75

4.2 mi away

0.6 mi long · Easy · Orlando

Hiking Biking Paved

408

4.3 mi away

0.3 mi long · Easy · Conway

Hiking Biking Paved

0.9 mi long · Easy · Altamonte Springs

Hiking Biking Paved

3.5 mi long · Easy · Azalea Park

Hiking Biking Paved

Gertrude's Walk

4.6 mi away

0.6 mi long · Easy · Orlando

Hiking Biking Paved

1.4 mi long · Easy · Orlando

Hiking Biking Paved

Cranes Roost

5.4 mi away

1.0 mi long · Altamonte Springs

Hiking

1.2 mi long · Easy · Orlando

Hiking Biking Horses Paved

Lake Lawne Trail

6.0 mi away

1.4 mi long · Easy · Pine Hills

Hiking Biking Paved

Nearby cities

Walking trails in Florida

Common questions

How many walking trails are near Winter Park?
We list 197 walking trails within 30 miles of Winter Park, Florida. This page shows the 30 closest.
What is the longest walking trail near Winter Park?
Little Econ Greenway is the longest on this page at about 7.2 miles, 3.4 miles from Winter Park.
Are there dog-friendly trails near Winter Park?
None of the trails on this page have a dog rule in our data yet. Check signs at the trailhead or the park's website.