Trail Running calendar near Brooksville 2026-2027

Hit the Pinellas Trail for a Halloween-themed run supporting veterans. The Camo & Cobwebs event offers a timed 5K and an untimed 1 Mile Fun Run/Walk, both starting and finishing at de Bine Brewing Company. Expect costumes, finisher medals,..

Experience an off-road 5k trail run with your dog at Rock Springs Run State Reserve. This dog-friendly event features a spooky theme, finishers medals for both humans and pets, and supports local animal rescues.

This Halloween trail race offers a spooky evening on the Florida Greenway. Choose from 5k, 10k, or a combined challenge in either run or ruck divisions. Costumes are encouraged, and all finishers get a medal.

Celebrate Halloween with a spooky 5K in Clermont. The evening event features haunted zones, a costume contest, and a live DJ. A virtual 5K option is also available.

Experience the natural beauty of Florida at Lake Louisa State Park with trail races across rolling sandhills and shaded oak hammocks. Choose from three distances featuring scenic lakeside views and diverse forest terrain.

Celebrate Thanksgiving with a series of themed races including a Half Marathon, 10k, and 5k in Orlando. Enjoy chip timed results, finisher medals, and family friendly distances like the Kids Dash and 1 Mile fun run.

Join this patriotic honor run on the scenic Pinellas Trail to celebrate military veterans. Choose from 10K, 5K, or Kids Dash distances in a stroller friendly environment at Dunedin.

Celebrate Thanksgiving with this family friendly event in Tampa featuring distances from a Kids Dash to a Half Marathon. Enjoy chip timed results, finisher medals, and festive treats at the finish line.

Experience an obstacle course event in Dade City Florida featuring 3.5 mile and 6.2 mile distances. Choose between competitive pro waves, open divisions, or a ruck category for a unique outdoor adventure.

Honor America's veterans at this scenic out and back race along the paved Courtney Campbell Causeway Trail. Choose from multiple timed distances and enjoy panoramic views of Tampa Bay while supporting veteran suicide prevention.

Explore Tampa Bay on foot in this unique 100-mile urban tour. The point-to-point route winds from Ybor City to St. Petersburg, passing murals, beaches, and city landmarks. It's a self-reliant adventure with a 36.5-hour cutoff to earn your f..

Experience the natural beauty of Lakeland at Colt Creek State Park for a trail event featuring distances from 14 miles to a 60 mile ultra. Enjoy a loop based course with handcrafted medals and a post race picnic.

Experience a team relay through the shaded pine forests and palm trees of Alafia River State Park. Run together in teams of four or eight and enjoy a festive weekend village with campfires and star lit camping.

Celebrate the holidays at the Candy Cane Course in Orlando featuring distances from a Kids Dash to a 15k. Enjoy chip-timed results, designer shirts, finisher medals, and festive treats at the finish line.

Holiday races in downtown Dunedin at HOB Brewing Company offer 5K, 10K (2 loops) and 15K (3 loops) on a paved, timed course along the Pinellas Trail, with medals, event shirts and a post-race beer for participants over 21.

Celebrate the season at this Christmas themed run in Tampa featuring 15k, 10k, 5k, and kids distances with custom medals and festive treats for all finishers.

The Long Haul 100 is a Western States qualifying trail race in Florida's Colt Creek State Park. Runners can tackle a 100-mile loop course or a shorter 12.5-mile option on the scenic trails.

This free 12-hour event invites participants to run or walk as many 5-mile loops as they like on shaded trails. Enjoy a social, laid-back atmosphere with a community potluck aid station. Everyone completing at least 10 miles receives a fini..

Experience the natural beauty of Florida at Lake Manatee State Park. Run unique 5K or 10K dirt and sand trails while spotting local wildlife like gopher tortoises and armadillos.