Florida
Florida Trail Running Calendar 2026-2027
Explore the best trail runs in Florida for 2026-2027! Our updated list features 202 exciting trail runs across the region. Find your next trail run in Florida below and join the trail community at these great events!
January 2027
Trail races in Middleburg, FL offering 50K, marathon, 12K and 7K on diverse single track with views, stream crossings and on-course aid stations.
A 5K at Florida Horse Park combining road and grass terrain, benefiting the Foundation for the Horse, with in-person and virtual participation options.
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.
Fourth annual Wagging Tails on the Trails at Pepper Park Riverside features 5K and 9K trail runs along mangroves, a free Puppy Dash for ages 10 and under, and dog-friendly amenities including water stations and finish-line treats for dogs.
A trail event at Lake Manatee State Park on February 6, 2027 with 5K and 10K courses through dirt paths, sand and pine corridors. The race features chip timing, finisher medals, post race snacks and age group awards.
Trail races at Bone Valley ATV Park include a 10K, 5K, and a 1 mile color run on hilly, uneven trails. Back to back challenge options require an 18 minute per mile pace and awards are given by age category.
A last person standing race at DuPuis Management Area in Canal Point, FL on Feb 6, 2027, run on repeated 4.166667 mile loops with proceeds supporting the Loxahatchee FTA.
A fundraising 5K in Ormond Beach with in-person and virtual options. Proceeds benefit The Heterotaxy Connection and registration includes chip timing, a shirt, and a finisher medal.
A 5K and 10K run through an active limestone quarry in Miami with general, employee, and student categories; proceeds benefit Castaways Against Cancer.
A flat, two-loop 5K at River Ridge High School in New Port Richey supporting the school's cross country and track programs, with bobblehead awards and optional race shirts.
Morning trail races at Colt Creek State Park on February 7, 2027, offering a 5K, 10K, or the 15K Nighthawk Challenge with race shirt and finisher medals.
A multi-day ultrarunning festival in Middleburg, FL with 3 hour to 48 hour races, relays, a runner village, single-loop aid station, onsite medical support, and hot food.
Test your endurance at Coldwater Creek by completing ten 5k runs over 24 hours. Navigate single track trails and sandy roads while enjoying provided hot meals and on site camping at this unique ultra distance challenge.
Trail races and a virtual option follow the Lake Apopka North Shore Loop Trail from Magnolia Park, with distances from 5K to 30K, cupless format and required personal hydration.
A community running and walking event on the paved Blackwater Heritage Trail in Milton, FL, offering a 13K race with awards, a 2.7 mile fun run/walk with prizes, para divisions, and a shirt purchase option.
A 10.25 mile trail race in Naples Florida on Feb 13 2027 with mixed terrain, age group awards, prize money, and a Legacy entry for five-time finishers; no dogs allowed.
A 5K in Ocala on mixed road and trail terrain with age group awards, a Sweetheart team division, and proceeds supporting Vanguard High School cross country.
Trail ultrarun in the Green Swamp near Dade City, FL offering 60K, 30K and a 30K ruck with marked trails, regular aid stations, and finisher hats.
Trail run and walk at Seminole State Forest in Sorrento on Feb 14, 2027, with 5K, 12K, half marathon distances and a tracked chair category.
A Valentine’s Day 5K at Southern Hills Farm in Clermont with chip timing, finish line chocolate treats, and kids dashes.