Trail Running calendar near Tampa 2026-2027

Run or walk through the scenic orchards and vineyards of Formosa Winery in Kissimmee. Participants enjoy chip-timed results followed by cider and homemade donuts at this unique venue near Walt Disney World.

Join the festive St. Patrick's Day run in Dunedin on the flat, paved Pinellas Trail. Choose from a 5K or 10K course, both starting at HOB Brewing Company. The event includes a medal, tech shirt, and a post-race party in a family and pet-fri..

Celebrate 30 years of trail running at the Croom Fools Run in Florida's Withlacoochee State Forest. Choose from a 50 miler, 50K, or 16 mile race on a scenic, looped course through pine forests and rolling hills. All finishers get an award,..

Experience flat trail races through the scenic pines and lakes of Colt Creek State Park. Choose from a 5K, 10k, or Half Marathon with chip timing and a competitive run club challenge.

Experience a paved loop course around the salt mines of SunWest Park in Hudson. This memorial event offers timed 10K and 5K races alongside an untimed 5K walk or run to support local adaptive park programming.

Kick off the Dunedin Highland Games with this 5K trail run and walk. The scenic course starts and finishes at Highlander Park, venturing into Hammock Park. Registration includes a t-shirt, medal, and entry to the festival with Celtic music..

Join the Kraken in Sarasota for a 5k or 10k race featuring finisher bottle openers and t-shirts for all runners. Enjoy a community event with awards for top performers across multiple age groups.

Join the fun at the DoNot Stop running event in Orlando, a donut-themed race with options from a kids dash to a half marathon. Every finisher gets a custom medal, event shirt, and a free donut. The event features chip timing and a virtual o..

Tackle the rolling hills and sandy trails of an old phosphate mine at the Funest 50K. This event offers 50K, 30K, and 10K distances on a challenging 10K loop course in Loyce E. Harpe Park. Runners can enjoy post-race food and support trail..

Experience a unique sunrise run on the beautiful sands of Englewood Beach featuring a 5K and 1 Mile fun run. All finishers receive a custom sea turtle beach towel and a special magnetic medal.

Experience the 3rd annual Race for the Planet 5K at Babcock Ranch. Enjoy a scenic route through trails and sidewalks in Punta Gorda with timed and untimed options for all participants.

Experience a loop based trail race through the scenic horse and hiking paths of the Withlacoochee Forest. Choose from marathon, half marathon, or 10K distances and enjoy primitive camping at the venue.

Run through 250 acres of pristine woods and shaded hammocks in Punta Gorda. This event features trail races for various distances and a kids fun dash to benefit the Gator Wilderness Camp School.

The Stomp Out Suicide Trail Race is a scenic event on May 2, 2026, in Dade City. It features a 10K, 5K, and 1-mile run/walk on shaded trails to raise awareness for suicide prevention. All participants get a shirt, snacks, and a finisher's a..

Tackle a scenic single-loop trail course through Florida's Withlacoochee State Forest. Choose from a 50K, 25K, or 10-mile race, all starting and finishing at Holder Mine Campground. Expect full support, a post-race picnic, and a custom awar..

Run the trails of Croom Park at night in this unique evening event. Choose from three distances on a marked 7-mile loop. A headlamp is required to experience this nocturnal trail run.

A trail running event in Clermont Florida on June 13, 2026 offering 4 mile and 8 mile distances with leftover medals and swag, post race food and awards, plus live music and professional timing.

A 5K at Robinson Preserve in Bradenton on June 13, 2026, offering participant t-shirts, snacks and post-race hotdogs, age-group awards for male and female finishers, and a guided pre-race stretch session.

A 30 km night trail run through the diverse and wildlife-rich terrain of Florida's Green Swamp. The event features a supportive atmosphere with no time cut-off and a festive post-race potluck. It's part of a larger trail series and is marke..

Experience the Withlacoochee Forest after dark in this night trail race featuring 5, 10, and 20 mile distances. Navigate single track trails under the stars with glow stick markers and a post race picnic celebration.