Dade City
Trail Running Calendar near Dade City 2026-2027
Explore the top trail runs near Dade City for 2026-2027! We've gathered 32 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
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 with 5K, 10K and half marathon courses through pine forest and lakeshore plus team and age-group awards.
An obstacle-race day in Dade City on Nov 14, 2026 offering full 5–7 mile Savage Race, a 3-mile Blitz, kids courses, spectator passes, and paid parking.
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
Course preview and training run on December 5, 2026 in Lakeland FL. One loop of 16.8 miles with marked turns, water-only aid stations, and primitive camping available.
January 2027
Trail races at Croom Park near Brooksville FL with 50K, 20 Mile and 10 Mile on a 10 mile loop and aid stations about every five 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.
A six-hour trail challenge in Clermont, FL where runners complete a 5K each hour for up to six rounds, earning patches, a medal, and leaderboard placement.
A six hour trail challenge in Lakeland where runners complete a 5K each hour, earn patches or a medal for finishes, and compete for local and world leaderboard rankings.
February 2027
A Valentine’s Day 5K at Southern Hills Farm in Clermont with chip timing, finish line chocolate treats, and kids dashes.
March 2027
Trail races on March 6, 2027 at Ridge Manor Trailhead near Brooksville, FL featuring 33 1/3 mile, half marathon and 6K courses through the Croom Tract.