Trail Running calendar near Williston 2026-2027

Celebrate the new year with Westly's 9th Annual 5K in Oakland, Florida. Run or walk the in person West Orange Trail event or join virtually anytime in January for a free, family friendly 5K with post race festivities and live music.

Join the Night Owl 5K, Coyote 10K or the Nighthawk 15K challenge at sunset on Colt Creek State Park trails. Expect rugged terrain and a required headlamp for the 5K, plus shirts and medals for all and an extra medal for challenge finishers.

Experience the Sombrero Ultra Running Festival in Middleburg FL with races from 3 to 48 hours, live music, vendors, and themed giveaways. Bring your crew and enjoy a runner village, a single aid station, medical support, and awards.

A trail ultramarathon at Green Swamp near Dade City on February 14, 2026 offering 60K, 30K and a 30K ruck over varied Florida terrain, regular aid stations, a pet food drive and finisher hats.

Run or walk the scenic Lake Apopka trails from Magnolia Park on February 15, 2026, with 30K, 8 mile, 5K and a virtual option. Enjoy varied trail surfaces, a tech shirt and medal, and post race food in a wildlife friendly, cupless event.

Trail trail event at Manatee Springs State Park in Chiefland, FL on February 21, 2026, offering 5K, 10K and a half marathon through cypress trees with spring water views and possible manatee sightings. The field will be capped.

Join the 39th Real Florida 5K 10K at Wekiwa Springs State Park for a scenic off road run through natural Florida. Choose 5K or 10K, enjoy a capped field for a relaxed race vibe and a tech shirt and finisher medal for all entrants.

Trail races of 25K and 50K in Cary State Forest near Bryceville, FL on Feb 21, 2026. Flat forest roads, aid stations, post-race lunch, and proceeds support Florida Striders Kids' Running Programs.

Trail races of 10K, 30K and 50K plus a new 50K relay take place in Palm Coast, FL on February 21, 2026. The 50K includes 2,345 feet of elevation gain, and the 10K raises funds for breast cancer research.

A navigation-heavy, self-supported urban loop in Ocala featuring painted-horse artworks and two distance options. The untimed event emphasizes route-finding and sightseeing rather than racing.

A family-oriented 5K trail run at Silver Springs State Park on February 28, 2026, featuring a children's area, refreshments, age-group medals, team awards, and proceeds that fund local septic maintenance grants.

The Gator Dash Trail Run will take place in Southwest Jacksonville on Sunday 1 March 2026. You can run between 10 and 21 kilometers.

A single loop trail event near Brooksville, Florida, offering 33.3 Miler, Half Marathon and 6K options with marked trails, aid for longer distances, finisher awards and a post-race picnic.

Run the 1st Annual Archie's Pizza Mile Trail Style in Williston FL on March 7 for a lively three loop beer mile with a non alcoholic option and finisher medals. Trail running, pizza vibes, and awards for overall winners.

A no-fee ultra in the Ocala National Forest offering 50K and 30K options along the Florida Trail, capped at 50 entrants and routed through Juniper and Hopkins Prairies.

A youth trail run at Princess Place Preserve on March 21, 2026, with races for ages 3 to 13 over three distances. The flat, mostly hard-packed course offers timing, wooden finisher medals, water stations, and age-group awards.

Lace up for the FTC Archer Braid Trail 5k & 10k in Archer, Florida, a flat, paved out and back through peaceful countryside. Choose 5k or 10k, enjoy timed results, age group awards, and a midcourse hydration stop.

Hit the trails at Paynes Prairie Preserve on March 28, 2026 for the Trail of Payne featuring 5k, 10k and a 1 mile fun run. New course winds through varied terrain from soft sand and roots to sunny prairies and shady forest.

Trail runs at Silver Springs State Park on March 29, 2026 include a half marathon, 10K, 5K and a virtual option, with a tech shirt, finisher medal, and awards for top finishers.

Run the 30th Croom Fools Run in Withlacoochee State Forest near Brooksville, FL, with 16 mile, 50K and 50 mile options on a scenic 16 mile loop. Limited field and a laid back post race picnic make for a classic trail day.