Dade City
Trail Running Calendar near Dade City 2026-2027
Explore the top trail runs near Dade City for 2026-2027! We've gathered 25 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
Complete as many 2.84 mile laps as possible around Lake Hollingsworth in this 6 hour or 12 hour endurance challenge featuring a full hot food menu.
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.
Second annual Withlacoochee River 5K Run/Walk in Dade City on Oct 17 2026 with live 5K, 1 mile and virtual 5K plus medals, awards and charitable giving.
A Halloween 5K in Clermont with haunted spook zones, a costume contest, and a live DJ. A virtual 5K option includes shirt, bib, medal and domestic shipping.
November 2026
A chip-timed trail run at Lake Louisa State Park on November 7, 2026 offering 5K, 10K and half-marathon distances with aid stations and on-course restrooms.
Obstacle races in Dade City, Florida on November 14, 2026, with a 3+ mile 15 to 20 obstacle course or a 5 to 7 mile 25+ obstacle course.
A Brooksville race day on November 21, 2026 with a 5K trail run, a 2.5K costume turkey trot, and a 0.8K color run supporting local Scouting programs.
Thanksgiving themed 5K and kids dashes at Southern Hills Farm in Clermont with chip timing, finisher medals, free local coffee and apple cider donuts.
Turkey Day 5K Clermont is a Thanksgiving themed 5K at Waterfront Park in Clermont, FL, featuring finisher medals, race swag, and an out-and-back course on the Upper Tampa Bay Trail.
December 2026
Course preview for the 2027 LH100 at Colt Creek State Park in Lakeland, FL featuring a single 16.8 mile loop, primitive camping, and unstaffed water stations.
January 2027
Trail race in Brooksville FL offering 50K, 20M and 10M on looped courses through Croom Park in the Withlacoochee State Forest.
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.
Six hour trail challenge in Clermont where runners complete a 5K each hour; four and five laps earn patches, six laps earn a medal and national leaderboard ranking.
February 2027
Valentine's Day 5K at Southern Hills Farm in Clermont with chip timed 5K, chocolate treats at the finish, and kids dash options for families.