Florida
Florida Trail Running Calendar 2026-2027
Explore the best trail runs in Florida for 2026-2027! Our updated list features 196 exciting trail runs across the region. Find your next trail run in Florida below and join the trail community at these great events!
November 2026
A Veterans Day running event in Dunedin offering a 5K, a two-loop 10K and a kids Honor Dash on the paved, stroller friendly Pinellas Trail with American themed finisher medals and timed results.
Women only 5K beach run/walk at Jacksonville Beach Seawalk Pavilion on Nov. 8, 2026, with chip timing, awards, a festival village and concerts after the race.
Three hour in person trail run in Big Cypress near Ochopee FL, organized by Bearly Runners with meetup at Cross Seminole Trail Entrance.
Across Florida 200 is a fully supported 200 mile point to point trail run from Yankeetown to St Augustine held Nov 11–15, 2026 with a 96 hour cutoff.
Obstacle-course event in Dade City FL on November 14, 2026 with a 5 to 7 mile race, a 3 mile blitz, kids courses, spectator access and parking options.
Experience a scenic trail run through the long leaf pines of Blackwater River State Forest. Enjoy a post race BBQ and the opportunity to swim in Krul Lake after completing the half marathon course.
Veterans Run in Tampa features 5K, 10K, half marathon and 15.5 mile out and back races plus virtual options along the Courtney Campbell Causeway.
A family mud obstacle event in Ave Maria, FL on Nov 14, 2026 where parents and children complete the same 1.5 to 2 mile lap together, ages 5 and up, no clock.
A well marked 5K loop on the Florida Trail in Ocala with running and rucking divisions, live timing, race day packet pickup, and a custom finisher medal; ruck entrants must meet specific weight and pack rules.
A family friendly 5K color run at St. Johns County Fairgrounds on November 14, 2026, with a $25 entry that includes a shirt and medal; free registration for ages 2 and under.
A community 5K trail run and walk at Riverbend Park with in-person and virtual options, raising funds for the Sari Center's cancer support services.
A 5K trail race at Halpatiokee Park in Stuart, Florida, organized by the Cooper Steadman Foundation to raise funds for families of children with childhood cancer.
A community 5K at Rye Preserve in Parrish, FL with mixed terrain, a free kids Fun Run, organized warm ups and yoga, and a portion of fees donated to Foundation for Dreams.
Oceanfront 10K and 5K beach races at Anastasia State Park with virtual and shirt-only options; the event supports two local charities and includes a race packet with shirt, medal and bag.
Multiple-loop trail races at Colt Creek State Park on November 21, 2026 offering distances from 14 miles to 60 miles with three aid stations per loop.
A 10-mile night trail run at Jonathan Dickinson State Park, run on a marked lollipop loop through pine flatwoods and sand scrub. Registration includes park entry, a shirt, a finisher medal, and post-race refreshments; space is limited.
A backyard ultra at San Felasco where runners complete repeating 4.167 mile loops each hour until one competitor outlasts the others.
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.
Thanksgiving fun run at Donna Fiala Eagle Lakes Community Park in Naples with a 2.25 mile loop, prizes include a ham for the winner and a turkey for the first to complete two laps.