Trail Running calendar near Williston 2026-2027

Take on the Monroe Cross Trail Ultra in DeBary, Florida offering 50 mile, 50K and 17K options along scenic paved multi use trails. The point to point 50 mile starts in Edgewater and finishes at Central 28 Beer Company with aid stations, med..

This Ain't Your Mothers 50K and Trail Marathon on January 25, 2026 in Middleburg Florida offers single track, waterfalls, stream crossings and scenic vistas on the Pioneer Trail. Choices from 7K to 50K suit racers and adventurers.

Run a scenic 5k through Masaryk Winery vineyards with chip timing and a festive wine themed finish. Receive a tee, shatterproof collapsible wine glass and a finisher medal that doubles as a wine stopper while supporting Nik's Wish.

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.

Skunk Ape’s Revenge is a rugged trail run at Green Swamp West Tract in Dade City offering 60K, 30K and a 30K ruck option. Enjoy sandy single track, dirt roads and rolling hills, plus camping and a pet food drive for the local community.

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.

Discover Manatee Springs on Saturday Feb 21, 2026 with scenic trail races through springs fringed by cypress where you might spot manatees. Choose a half marathon, 10K or 5K and enjoy nature, but entries are limited so sign up early.

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.

Celebrate the Angry Tortoise's 13th anniversary at Cary State Forest on Feb 21 2026 with flat, fast trail courses in 25K and 50K. Well supported aid stations, post race lunch, and scenic forest roads make for a fun day.

Experience single track trails at the Swamp Trail Race in Palm Coast, Florida on Feb 21, 2026, with distances from the breast cancer fundraiser Debby 10K to a tough 50K and a new 50K relay. A small field creates an intimate, friendly race v..

Join the Painted Horse Urban Ultra in Ocala on Feb 21 for a self supported, navigation heavy adventure. Choose 55k or 25k routes that visit dozens of painted horse sculptures, and it is not a race but a sightseeing scavenger hunt.

Join the family friendly Run for the Springs 5K through scenic Silver Springs State Park trails on Saturday Feb 28, 2026. Enjoy a kids area, refreshments, door prizes, age group medals and a Traveling Cup for the fastest team.

Challenge yourself at the Jacksonville Trail Experience at Diamond D Ranch, an early season Spartan Trail that blends fast, runnable sections with muddy, ankle biting terrain. Choose 10K or 21K to test speed and grit.

Run scenic single loop trails along the Withlacoochee River in the Croom Tract with options from 6K to the challenging 33.3 mile distance. Enjoy aid stations, a post race picnic and a quirky vinyl record finisher award.

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.

Two Prairies Ultra is a low key FAT ASS on the Florida Trail near Salt Springs, FL, with 50K and 30K options through scenic Juniper and Hopkins Prairies. Limited to 50 runners and encourages a trail donation; register by March 7.

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.