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!
November 2026
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.
First annual Kilted 5K walk and run in Dunedin with a trail through Hammock Park; entry includes a T-shirt, medal, and admission to the Dunedin Celtic Festival.
Five hour trail event at Sal Taylor Creek Preserve in Jacksonville with a four to five mile loop, charity donations for Sombrero Outreach Foundation, food and random giveaways.
Charity 5K in Tallahassee on a flat shady course of paved and dirt trail, where well behaved dogs on non retractable leashes may run and canine awards are given.
A 5K trail run/walk at Otter Springs in Gilchrist County on 21 November 2026 with youth and adult divisions and proceeds supporting local high school athletics.
A family-focused Thanksgiving 5K at Southern Hills Farm with chip timing, kids dashes, on-course entertainment, and local food offerings.
Beach 5K in New Smyrna Beach on November 26, 2026 with chip timing, finisher medal, race shirt, water stations, and an after-race celebration at Flagler Tavern.
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.
Thanksgiving morning 5K on the paved Upper Tampa Bay Trail in Tampa with costumes encouraged, finisher medals, music, and family-friendly activities.