Trail Running calendar near Osteen 2025-2026

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.

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..

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..

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..

Take on Skunk Ape’s Revenge at Green Swamp West by choosing 60K, 30K or a 30K Ruck and tackle sandy trails, single track and dirt roads through wild Florida scenery. Bring pet food for Cindy’s Pets and earn a finisher hat.

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..

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 returns Saturday, Feb 28, 2026 at Holloway Park in Lakeland FL, featuring 50k, 30k, 10k and a five person 50k relay on fast groomed 10k loops. Enjoy a mix of trail and road like sections on a well maintained course.

Run scenic single track through Withlacoochee State Forest along the river at the Long Play Trail Run in Brooksville, Florida. Choose 33.3 miles, a half marathon or 6K and finish with a vinyl record and post race picnic.

Run the Two Prairies Ultra in Ocala National Forest near Salt Springs, choose 50K or 30K on scenic out and back routes through Juniper and Hopkins Prairies. Entry is limited to 50 runners and a suggested donation supports the Florida Trail.

Celebrate St Patrick spirit at the Time to Paddy 5k/10k and Lucky 13.1 in Orlando with in person and virtual options for every pace, from a 1 mile and kids dash to a half marathon. All finishers get a designer shirt and custom medal.

Celebrate the 30th annual Croom Fools Run on scenic trails through Withlacoochee State Forest, with 16 Mile, 50K, or 50 Mile loop courses, full aid stations, and a laid back post race picnic. Field is limited to 250 runners, so register ear..

Run scenic trails at Colt Creek State Park with 5K, 10K, or half marathon options, chip timed and featuring event swag, a finisher medallion, and post race snacks. Awards for overall, age groups, and teams make this a fun day for solo runne..

Run the scenic Withlacoochee Trail Marathon through shaded hiking and horse trails near Lecanto, FL, with marathon, half marathon and 10K options. Enjoy aid stations, a finisher shirt and post race food amid peaceful forest scenery.

Skunk Ape Trail Race in Ocala invites runners to tackle 50 mile out and back or the double loop 100 mile challenge through scenic Cross Florida Greenway. Expect sandy single track, night miles with glow lights and stocked aid stations.