Looking for the best trails around Holiday?

Explore the best rated trails in Holiday, FL, whether you're looking for an easy walking trail or a bike trail like the Withlacoochee State Trail and Coastal Anclote Trail . With more than 29 trails covering 352 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 Holiday

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Showing 0 of 29
2 Reviews
Bayshore Trail

Although short, the Bayshore Trail provides an important connection between two popular trails on Florida's west coast: the Courtney...

Length: 0.9 mi
State: FL
Surface: Asphalt
4 Reviews
Bayway Trail

The Bayway Trail is a 3.7-mile non-motorized trail between St. Petersburg and St. Pete Beach, Florida. The trail begins its westward...

Length: 3.7 mi
State: FL
Surface: Asphalt
5 Reviews
Clearwater Memorial Causeway Trail

The Clearwater Memorial Causeway Trail is a paved 3.5-mile trail that connects Clearwater Beach and downtown Clearwater. About the...

Length: 3.5 mi
State: FL
Surface: Asphalt
9 Reviews
Coastal Anclote Trail

The Coastal Anclote Trail is a 4.5-mile multi-use path in southeast Pasco County, Florida. The paved trail includes one longer route and...

Length: 4.5 mi
State: FL
Surface: Asphalt, Boardwalk
60 Reviews
Courtney Campbell Trail

The Courtney Campbell Trail provides pedestrian and bicycle access along the southern side of the Courtney Campbell Causeway for nearly 11...

Length: 10.9 mi
State: FL
Surface: Asphalt, Concrete
2 Reviews
Crosstown Trail

The Crosstown Trail in Crystal River is a historic railway line that has been converted into a multiuse trail stretching nearly two miles.

Length: 1.8 mi
State: FL
Surface: Concrete
7 Reviews
Druid Road Trail

The Druid Road Trail is a vital link in Pinellas County’s extensive trail system, connecting two of its most prominent trails: the Pinellas...

Length: 4 mi
State: FL
Surface: Asphalt
15 Reviews
Duke Energy Trail

Please note: There is a gap in the route where it will cross over Lake Tarpon Outfall Canal. The bridge is scheduled for completion in...

Length: 11.68 mi
State: FL
Surface: Asphalt, Concrete
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

Recent Trail Reviews

Coastal Anclote Trail

Fun Skate Trail

August, 2025 by brookeypav

Super fun trail connecting three parks. Great for inline skating. Very smooth asphalt. Just a few road crossings. Very nice to see the Gulf. Definitely recommend to all the skaters !!!

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.

Good Neighbor Trail

warning

June, 2025 by dbrunoehler

always a great trail. so well maintained and marked. hence why we were surprised to encounter the large pile of sand close to marker 6160. both our bikes fishtailed. 3 other bikers were stopped. 2 others went to the highway to avoid.

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