Trail Running calendar near Holiday 2026-2027

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.

Experience a scenic trail race through the Carlton Reserve in Venice with distances ranging from 5k to 15k. Enjoy post race snacks and unique handmade wood awards in a festive community atmosphere.

The Long Play Trail Run will take place in Brooksville on Saturday 6 March 2027. You can run between 6 and 33 miles.