Brooksville
Trail Running Calendar near Brooksville 2026-2027
Explore the top trail runs near Brooksville for 2026-2027! We've gathered 12 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
September 2026
A trail half-marathon event in the Green Swamp West Tract offering a run and a ruck division, aid station at the turnaround, finisher glassware, and a post-race potluck.
October 2026
The John Holmes Trail Run takes place at Croom Park and Withlacoochee State Forest on October 3, 2026, offering 50K, 16 mile and 9 mile options. The field is limited to 250 runners and this is the event's 34th running.
November 2026
Savage Race in Dade City Florida on November 14 2026 features a 3 plus mile course and a 5 to 7 mile course with multiple obstacles; parking is $20.
A set of runs on November 21, 2026 in Brooksville, Florida features a 5K trail run, a 2.5K Turkey Trot with costumes encouraged, and a short Color Fun Run with colored powder. Proceeds support Scouting programs.
December 2026
January 2027
A chip timed 5 km run and walk at Masaryk Winery in Masaryktown, Florida on January 16, 2027, with a helper registration option, race items including a t-shirt and wine glass, and results posted online by J3 Timing.
February 2027
A 12-hour, donation-supported trail run at Whispering Pines Park featuring a marked 5-mile loop through shaded single- and double-track trails. Participants may complete as many laps as they wish and receive an award after two loops.
March 2027
Experience a unique single loop trail run through the Withlacoochee State Forest featuring 33 1/3 mile, half marathon, and 6K distances. Enjoy riverside trails and celebrate your finish with a post race barbecue and handcrafted medals.
April 2027
Trail marathon, half marathon, and 10K on unpaved Withlacoochee State Forest trails with three aid stations and mandatory personal hydration; primitive camping is available near the course.
May 2027
Stomp Out Suicide is a shaded trail run and walk at Withlacoochee River Park on May 15, 2027, offering 10K, 5K and 1 mile distances and focusing on raising awareness about suicide; participants receive shirts, snacks, and finisher awards.