Trail Running calendar near Holiday 2026-2027

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 the natural beauty of Florida at Colt Creek State Park with a chip timed trail run through pine forests and meadows. Choose between a 5K, 10K, or Half Marathon featuring finisher medals and a post race celebration.

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..

Enjoy a donut themed race in Tampa featuring distances from a Kids Dash to a Half Marathon. Participants receive custom medals and a fresh donut at the finish line.

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.

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 the rugged beauty of Florida at the Withlacoochee Trail Marathon. Explore scenic sandhills and oak forests on natural trail loops with marathon, half marathon, and 10K distances available.

Experience the heart of Florida on a 100 or 50 mile journey through the historic Marjorie Harris Carr Cross Florida Greenway. This endurance run features scenic pine forests, diverse wildlife habitats, and a supportive trail community.

Join this scenic trail race at Withlacoochee River Park to support mental health awareness. Runners and walkers can choose between 10K, 5K, and 1-mile distances through shaded Florida landscapes.

Experience an obstacle course race inside the iconic Raymond James Stadium in Tampa Bay. Navigate a 5K course with 20 obstacles through bleachers and past the famous pirate ship for a unique athletic test.

Test your endurance at Whispering Pines Park with a unique adventure race featuring a 5K run, swimming, and a Jeep push. Join as an individual or part of a team to support community wellness and educational initiatives.

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.

Join the Treat Trot at Gadsden Park in Tampa for a day of running with distances ranging from a Kids Dash to a 15K. Enjoy chip timed results, finisher medals, and free event photos in a scenic park setting.

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.

Experience a unique indoor backyard ultra where athletes run 5 miles every hour on Woodway treadmills. This Last Person Standing event features a climate controlled environment and a competitive field in St. Petersburg.

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 a summer running tradition in Tampa with distances ranging from a kids dash to a half marathon. Enjoy chip timed results and free ice cream at the finish line to stay cool.