Trail Running Calendar Florida 2026-2027

A second annual single loop trail event at Carlton Preserve in Venice, FL offering 50k, 25k, 5k and a youth 5k. The organizer provides event swag and Wicked Skin awards and registration closes January 29, 2026.

A multi distance trail event in Christmas, Florida on January 31 and February 1, 2026, offering 100 mile, 50 mile, 15 mile and 8 mile courses through Tosohatchee and other state forests. The routes feature single track, varied terrain, and..

Join the Pine Island Calusa Trail 5K on January 31, 2026 in Bokeelia, Florida for a scenic yet rugged trail run with solo, family and parent child entry options. Medals, post race refreshments and proceeds support Kiwanis youth programs.

A community 5K at Legacy Park in Venice, FL on January 31, 2026, with two age-based categories, chip timing, and post-race activities. Hosted by Respect 1st Responders to raise funds for Disaster Relief Kits; field limited to 200 runners.

Run the Ranch 5K in Sebring FL on Jan 31, 2026 invites runners and families to a scenic light trail course. Support Highlands County scholarships while racing at any pace and competing for age group medals.

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.

Celebrate Mardi Gras at Celery Fields with 5k, 10k and canicross races for runners and their dogs. Expect shirts, post race snacks, live music, vendors and age group awards plus a guided warm up.

Bring your leashed pup to Wagging Tails on the Trails at Pepper Park Riverside for scenic 5K and 9K trail runs, kids Puppy Dash, and a virtual 5K. Finishers get treats while proceeds benefit the St Lucie County Sheriff K9 unit.

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.

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.

Trail runs at Carlton Preserve in Venice on February 15, 2026 with 15k, 10k, 5k and a virtual race. The event includes a race t shirt, post race refreshments, music and age group awards.

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.

A multi-distance ultramarathon along Florida’s Space Coast and Treasure Coast with solo and 3-person relay options. Field limited to 100 runners and all events require support crew.

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.