Looking for the best trails around Cypress Gardens?

Explore the best rated trails in Cypress Gardens, FL, whether you're looking for an easy walking trail or a bike trail like the Withlacoochee State Trail and Orlando Southeast Trail . With more than 38 trails covering 332 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.

Best Trails in Cypress Gardens

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Showing 0 of 38
34 Reviews
Auburndale TECO Trail

The Auburndale TECO Trail is a 7.3-mile paved trail running between Polk City and Auburndale. About the Route The Auburndale TECO Trail...

Length: 7.3 mi
State: FL
Surface: Asphalt, Concrete
24 Reviews
Cady Way Trail

The Cady Way Trail is a 7.5 mile paved, multi-use pathway that runs between Orlando’s Coytown neighborhood and the Goldenrod area of nearby...

Length: 7.5 mi
State: FL
Surface: Asphalt
20 Reviews
Chain of Lakes Trail

The Chain of Lakes Trail stretches nearly 5 miles along an abandoned rail corridor between downtown Winter Haven and north of Lake Alfred...

Length: 4.7 mi
State: FL
Surface: Asphalt
57 Reviews
Cross Seminole Trail

Stretching from Orlando’s densely populated outskirts to the sleepy bedroom communities of Oviedo, Winter Springs, and Lake Mary, the...

Length: 29.4 mi
State: FL
Surface: Asphalt
0 Reviews
Dakota Avenue Linear Park

This short trail acts as a connector, delivering residents from their neighborhoods to the south shore of East Lake Tohopekaliga. The trail...

Length: 0.5 mi
State: FL
Surface: Asphalt
42 Reviews
Flatwoods Park Trail

The Flatwoods Park Trail is located within a park of the same name.  This multi-purpose route is a ten-mile paved loop that provides a...

Length: 10 mi
State: FL
Surface: Asphalt
28 Reviews
Fort Fraser Trail

The paved Fort Fraser Trail traverses part of the former CSX Railroad line, running parallel to US Highway 98 for 7.54 miles, between...

Length: 7.54 mi
State: FL
Surface: Asphalt
1 Review
Gaston Edwards Trail

In northern Orlando, the Gaston Edwards Trail provides a pleasant jaunt of nearly a mile along Lake Ivanhoe's eastern shore. (Hence, the...

Length: 0.7 mi
State: FL
Surface: Concrete
139 Reviews
General James A. Van Fleet State Trail

The General James A. Van Fleet State Trail runs for 29 miles between Mabel and Polk City through some of Florida’s most scenic rural...

Length: 29 mi
State: FL
Surface: Asphalt

Recent Trail Reviews

Flatwoods Park Trail

Peaceful trail

July, 2025 by rockieslights

We've ridden this trail for more than 20 years. Wildlife is a little more sparse these days, although we did see a deer and a turkey last week. It's a 7 mile one way loop (add 2 miles from the Bruce B Downs parking lot or 0.6 miles from the Morris Bridge Rd. entrance). It's in a fast growing area (New Tampa) but it doesn't take long to get away from civilization. There are some off road trails as well. It can get busy with fast riders and skaters. Parts of the main trail are going to need re-paving soon, but ample water stops and pleasant scenery make this one a lot of fun.

Seminole Wekiva Trail

Good Trail, could skip the very southern section

July, 2025 by joe511

I rode it down and back from Sorrento - part way into the Wekiva Trail. The trail is really nice in the middle - oaks, and parks, very pretty.
The southern end could be skipped as it has a lot of busy street crossing. A good place to start would be the Rooms To Go parking lot at mm 2.75.
There are2 tunnels under roads that are nice.
Street crossings could be marked better, need to pay attention when crossing - look for a No Vehicles sign and double yellow lines on the path at intersections (some are very faded). The path may jump sides or turn off, need to be attentive.

South Lake (Lake Minneola Scenic) Trail

beautiful ride

July, 2025 by lmu828

This is a beautiful ride with a very nice trail. Lots of cyclists, walkers, runners, and even roller blading. It’s very scenic and I felt safe by myself on this trail.

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