Trail Running calendar near Oakland 2026-2027

Find your pace on shaded trails at Wekiwa Springs State Park with timed loop races from 6 to 24 hours and a 24 hour relay option. Held January 3 to 4, 2026 in Apopka, Florida, the scenic 3.2 mile loop showcases wildlife and campsite support..

Croom Zoom is a scenic trail run in Brooksville's Croom Park through oak hammocks and tree canopy, with 50K, 20 mile and 10 mile options. Entries cap at 250, so register by January 1, 2026 to secure your spot and chase a finisher award.

Test your limits at the Long Haul 100 in Colt Creek State Park in Lakeland FL with a six loop 100 mile race or a 100 Furlongs loop. This Western States qualifier awards buckles and WSER lottery entry for finishes under 30 hours.

Monroe Cross Trail 50 Mile Ultra in DeBary, Florida offers 50 mile, 50K, and 17K on scenic paved multi use regional trails. The point to point 50 mile finishes at Central 28 Beer Company with finisher medals and prizes for top finishers.

Join the Masaryk Wine Run 5K at Masaryk Winery for a scenic vineyard run with chip timed results and free race photos. Participants get a tee, shatterproof collapsible wine glass, a finisher medal that doubles as a bottle stopper and a pour..

Forgotten Florida is a trail weekend near Oviedo and Christmas, FL offering 8, 15, 50 and 100 mile races through Tosohatchee and nearby state forests. Mostly single track trails and a community vibe with proceeds aiding trail conservation.

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.

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..

Run the Hunt for Sasquatch at Bone Valley ATV Park in Mulberry on Feb 7, 2026. Choose 10K, 5K, a color 1 mile or multi distance challenges, enjoy rugged trails and small hills, collect swag and celebrate at the finish line awards party.

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.

Run the Skunk Ape’s Revenge on February 14 in Dade City with 60K, 30K and a 30K Ruck across sandy single track, fire berms and dirt roads. Finishers get hats and stickers, top four men and women earn awards, and the race supports a pet food..

Run along the scenic Lake Apopka trails from Magnolia Park on February 15, 2026 with 30K, 8 Mile and 5K options plus a virtual race. Enjoy technical shirts, finisher medals and post race snacks while supporting local trail conservation.

Join the inaugural Longleaf Blaze Trail Run at Disney Wilderness Preserve in Kissimmee for scenic 5K and 10K trails through restored wetlands. Family oriented activities include a kids Gopher Tortoise Fun Run and finisher hats and medals.

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.

Run the Space Pirate 100 along Florida's Space and Treasure Coasts with distances from 33.3 mile to 100 mile solo or relay. Limited to 100 runners, all events are support crew only and finish on the beach with a treasure chest buckle.

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 at the Swamp Trail Race in Palm Coast, FL where 50K, 50K relay, 30K and the Debby 10K breast cancer fundraiser bring trail runners together. Field limited to 125 so register by Feb 18.

Join the Unicorns Among Us 5k in Ormond Beach on Feb 21, in person at Ormond Brewing Company or virtually. Enjoy a chip timed 5k with event shirt and medal, a free brewery pour with your bib, and support The Heterotaxy Connection.

Run through Ocala in the Painted Horse Urban Ultra, an untimed urban adventure and scavenger hunt with 55k and 25k loop courses visiting dozens of painted horse installations. Navigation heavy and mostly self supported.