Dade City
Trail Running Calendar near Dade City 2026-2027
Explore the top trail runs near Dade City for 2026-2027! We've gathered 24 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A trail half marathon and ruck through Green Swamp West Tract near Dade City with an out and back Florida Trail route and staffed aid at the turnaround.
Timed lap event at Lake Hollingsworth in Lakeland, FL offering 12 hour, 6 hour and 12 hour five-person relay formats on a 2.84-mile paved lap.
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.
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 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.
A Thanksgiving day event in Clermont with a chip-timed 5K that includes a shirt, medal, and apple cider donut plus kids races and a family-friendly post-race gathering.
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
Marked 16.8 mile course preview at Colt Creek State Park in Lakeland, FL with primitive camping and limited unstaffed water stops.
January 2027
Trail race in Brooksville FL offering 50K, 20M and 10M on looped courses through Croom Park in the Withlacoochee State Forest.
A multi loop 100 mile ultramarathon and a 12.5 mile 100 furlongs race at Colt Creek State Park on January 16 and 17, 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