Trail Running calendar near Kissimmee 2026-2027

Run the 30th Croom Fools Run in Withlacoochee State Forest near Brooksville, FL, with 16 mile, 50K and 50 mile options on a scenic 16 mile loop. Limited field and a laid back post race picnic make for a classic trail day.

Trail races at Colt Creek State Park on April 11, 2026 offer 5K, 10K and half marathon on well marked wooded trails. Aid stations, on-course restrooms, chip timing, finisher medals and awards are provided.

Trail races on mountain bike trails at Loyce E. Harpe Park in Mulberry, FL offering 10k, 30k and 50k loop formats. The course features sand and dirt trails with rolling hills, limited entries, and a portion of fees supporting Polk County pa..

The Withlacoochee Trail Marathon will take place in Holder on Sunday 19 April 2026. You can run between 10 and 42 kilometers.

Trail ultramarathon in Ocala, Florida with 50 and 100 mile options along the Florida National Scenic Trail, varied natural terrain, staffed aid stations, drop bag support, pacer rules for the 100 mile, and nearby campgrounds.

Join Stomp Out Suicide on May 2, 2026 at Withlacoochee River Park for a scenic trail run or walk that raises awareness for suicide prevention. Choose 1 mile, 5K or 10K routes and enjoy a race shirt, snacks and a finisher award.

A 57.41 mile point to point trail ultramarathon through the Ocala National Forest from Alexander Springs State Park to Rodman Reservoir Dam. Crew support and a communication device are mandatory and limited natural water requires planning.

Run the Turkey Creek 5K at Turkey Creek Sanctuary in Palm Bay on May 23, 2026 with in person or virtual options for runners and walkers. Enjoy race shirts, custom medals for the first 300 and post race refreshments.

Trail races of 50K, 25K and 10 miles in Inverness, Florida on single-loop courses through the Citrus Tract of Withlacoochee State Forest. Aid and hydration stations are provided and runners must carry their own hydration.

The Moon Over Croom will take place in Brooksville on Saturday 6 June 2026. You can run between 7 and 21 miles.

Run the Florida Run LEFTOVER Trail Race on June 13, 2026 at Lake Louisa State Park in Clermont, featuring scenic 4 and 8 mile trail courses. Professionally timed with awards, a leftover medal, live music and post race food for a family frie..

Experience the low frills Independence Double in Winter Park on June 27 to 28 with lap based 5K to 50K on a flat, shaded paved trail. Hand timed and cupless, the relaxed event suits self supported runners looking for simple aid and communit..

The Vero Beach Octopus Ultra uses eight out and back arms from a central base at the Environmental Learning Center, offering distances from a 5K to 100 miles. A 32 hour limit applies and crews are strongly recommended.

A night trail running event on July 18, 2026 in Green Swamp West Tract near Dade City, FL, covering 30K of varied Florida terrain with aid stations every 3 to 5 miles, finisher glassware, event stickers, and a post race potluck.

A night trail event at Holder Mine Campground in the Withlacoochee Forest offering 5, 10 and 20 mile single-track courses. Headlamps are required and courses are marked with reflective pins and glow sticks.

A point to point 50K on the Florida National Scenic Trail in Ocala, where runners navigate by orange blazes, must download the GPX and carry a phone, and can use on course aid and one drop bag location.

Join the PawPals 4 Life 5k on October 24, 2026 at Rock Springs Run State Reserve for an in person or virtual run that welcomes dogs and supports Pawfields Enrichment Group. Enjoy trail scenery, race swag, and medals for finishers.

Join the Nightmare on the Clermont Trails 5K on October 31 in Clermont, Florida for a spooky run or virtual 5K featuring interactive spook zones, live actors, and a DJ. Dress up for the costume contest, snag the new 2026 finisher bling, and..

Trail races at Lake Louisa State Park in Clermont offer 5K, 10K and half marathon routes through pine forests, lakeshores and meadows. Chip timed and welcoming to all, every finisher earns a medallion and age group prizes await.

A veterans focused race in Tampa along the Courtney Campbell Trail offering 5K, 10K, half marathon and 15.5 mile courses with virtual options, aid stations, a military discount code, and post race gatherings at Whiskey Joes.