Trail Running calendar near Orlando 2025-2026

Join the Time Travel Half Marathon in Tampa on Jan 11, 2026 with 5k, 10k, 1 mile and kids races plus virtual entries. In person runners enjoy a designer shirt, custom medal, chip timing and free photos for a lively finish line.

Tackle scenic Florida trails at Long Haul 100 in Colt Creek State Park, Lakeland. Choose the epic 100 mile challenge or a shorter 12.5 mile loop and enjoy wildlife, aid stations and a finisher buckle.

Run through time in Orlando at the Time Travel Half Marathon with 5K, 10K, half marathon, 1 mile and kids races, available in person or virtually. Timed distances feature chip timing, custom bib, designer shirt, finisher medal, free photos..

Take on scenic Volusia County trails on Jan 24, 2026 with 50 mile, 50K and 17K options starting or finishing at Central 28 Beer Company in DeBary Florida. Enjoy trail views, on course aid, postrace food and a beer to celebrate your finish.

Run or walk a chip timed 5k through the scenic vineyards at Masaryk Winery, then enjoy a shatterproof wine glass and a wine pour for eligible participants. Proceeds benefit Nik's Wish and finishers receive a bottle stopper medal.

Forgotten Florida is a multi distance trail weekend in Christmas, Florida on Jan 31 and Feb 1 2026, with ultras and shorter loops across palm groves, pine flatwoods and scenic single track. Spot herons, cranes and bald eagles while navigati..

Join The Couple Shuffle in Tampa on January 31, 2026 for a festive couples friendly race offering a Kid's Dash, 2 Mile, timed 5k, 10k and 15K plus a virtual option. Expect shirts, medals, chip timing and age group awards.

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..

Hunt for Sasquatch at Bone Valley ATV Park in Mulberry for a playful trail race with a chance to spot Sasquatch. Choose a 1 mile color fun run, 5K, 10K or multi race challenges and enjoy a t shirt, swag bag and awards.

Sunset trail run at Colt Creek State Park in Lakeland FL on Feb 7, 2026 with 5K, 10K, or the Nighthawk 15K Challenge completing both races back to back. Expect unpaved terrain, headlamps required for the 5K, finisher medals and a race shirt..

Run Skunk Ape's Revenge in Green Swamp, FL on Feb 14 with 60K, 30K and 30K Ruck options across sand, single track and rolling berms. Enjoy frequent aid stations, finisher hats, overall awards and support a pet food drive for Cindy's Pets.

Choose from 30K, 8 Mile, 5K or a virtual trail run, walk or bike along the scenic Lake Apopka trails starting at Magnolia Park. Enjoy lakeside views and birding, finisher medals and tech shirts, and remember the event is cupless so bring yo..

Family friendly trail run at Disney Wilderness Preserve in Kissimmee with 5K, 10K or Double Down options and a Gopher Tortoise Fun Run for kids. Hats and finisher medals provided; the race is untimed and cupless so bring hydration.

Run the Space Pirate 100 along Florida Space and Treasure Coasts from Cape Canaveral to Jensen Beach; choose the 100 Miler, 100 Miler 3 person relay, 50 Miler or 33.3 Miler. Field is capped at 100, support crew only, and finishers earn a bu..

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.

Run single track trails in Palm Coast on Feb 21, 2026 with distances from a challenging 50K, now offering a new 50K relay, down to a meaningful 10K fundraiser. The field is capped at 125 runners for a close knit trail experience.

Run a 5 km in person or virtual in Ormond Beach on Feb 21, 2026 to honor a child and support The Heterotaxy Connection. Registration includes a shirt, medal, chip timing for the in person race and a free pour at the finish.

Run Ocala's Painted Horse Urban Ultra, a low key, self supported navigation adventure from the Where's the Finish? Podcast on Feb 21 2026. Choose 55k or 25k loops that visit dozens of painted horses for a noncompetitive, unsupported adventu..

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 invites runners to a scenic cross country style course mixing trail and road at Holloway Park on Feb 28, 2026. Choose from a 10k up to a 50k or join a five person relay for a fun team challenge.