Dade City
Trail Running Calendar near Dade City 2026-2027
Explore the top trail runs near Dade City for 2026-2027! We've gathered 28 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
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.
An evening Halloween 5K in Clermont on October 31, 2026, with spook zones, a costume contest, a DJ, a kids' trick-or-treat trail, and a virtual 5K option.
November 2026
Chip-timed trail races at Lake Louisa State Park offering 5K, 10K and half marathon courses through pine forest and lakeshore with aid stations and team awards.
Obstacle course event on November 14, 2026 in Dade City FL with a 3+ mile BLITZ (15–20 obstacles) and a 5–7 mile race (25+ obstacles).
Trail and family runs at Sand Hill Scout Reservation in Brooksville, featuring a 5K, a costume 2.5K Turkey Trot, and a 0.8K Color Fun Run.
A family-focused Thanksgiving 5K at Southern Hills Farm with chip timing, kids dashes, on-course entertainment, and local food offerings.
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
A single-loop 16.8 mile course preview in Lakeland FL with unstaffed water stops and a reserved primitive campground the night before.
January 2027
Trail runs at Croom Park near Brooksville, FL offering 50K, 20M and 10M on a 10 mile loop with aid stations about every 5 miles.
Timed 5k at Masaryk Winery in Masaryktown, FL, with on-site wines, a finisher medal that doubles as a wine stopper, and race timing 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.
A six-hour trail challenge in Lakeland where runners complete a 5K every hour; finish all six laps to earn a medal, patches and a spot on the national leaderboard.
February 2027
Valentine's Day themed 5K at Southern Hill Farms in Clermont with chip timing, a shirt, medal and chocolate treats plus kids races and free coffee and ice cream.