Trail Running calendar near Brooksville 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..

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.

Race under the stars at AdventHealth Nighthawk Trail Run in Colt Creek State Park with 5K, 10K and a 15K Challenge. Rugged unpaved loops, headlamp required for the 5K, finisher medals and a race shirt promise a memorable night on the trails..

Join the Gopherdillo Trail Run at Lake Manatee State Park on Feb 7, 2026 for scenic 5K and 10K non loop courses over sand, grass and paved roads. Expect wildlife sightings, a performance shirt option, and a finisher medal.

Join The Hunt for Sasquatch at Bone Valley ATV Park on February 7, 2026 for a fun trail challenge over varied terrain and small hills. Choose from 10K, 5K, 1 Mile or multi race options, with shirts, swag and awards.

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.

A trail event at Green Swamp West Tract near Dade City offering 60K, 30K and a 30K ruck on varied Florida terrain with aid stations every 3 to 5 miles, finishers hats, and a local pet food drive.

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.

Join the inaugural Longleaf Blaze Trail Run at Disney Wilderness Preserve with 5K, 10K or Double Down options. Family friendly with kids activities, finisher medals and hats; bring your own water bottle and enjoy scenic trails.

Celebrate Mardi Gras on the flat, paved Pinellas Trail with 5K, 10K or 15K options hosted at HOB Brewing Company in Dunedin. Limited to 200 runners, all finishers get a medal and 21 plus registrants enjoy a complimentary beer.

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.

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.

Explore Lakeland on a 30k urban adventure visiting painted swans from the Swansation art trail while navigating with a race book. This low key, self supported run from the Where's the Finish? Podcast mixes city charm and relaxed challenge.

All Day at Holloway offers a well groomed cross country loop of trail and road at Holloway Park in Lakeland on Feb 28, 2026. Choose 10k, 30k, 50k or a five person 50k relay.

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.

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.