Trail Running calendar near Holiday 2026-2027

A 100-mile endurance run in the Marjorie Harris Carr Cross Florida Greenway near Ocala, Florida, held April 25-26, 2026, on mixed single-track and paved trails. The course is an out-and-back with staffed aid stations, drop-bag locations, a..

Join this scenic trail race at Withlacoochee River Park to support mental health awareness. Runners and walkers can choose between 10K, 5K, and 1-mile distances through shaded Florida landscapes.

A 5K Spartan Stadion at Raymond James Stadium featuring 20 obstacles, stadium stairs, and a kids race. Spectator options are available and the event is supported by local sports partners.

Test your endurance at Whispering Pines Park with a unique adventure race featuring a 5K run, swimming, and a Jeep push. Join as an individual or part of a team to support community wellness and educational initiatives.

Trail races of 50K, 25K and 10 miles on a single loop through the Citrus Tract in Withlacoochee State Forest near Inverness, FL. Marked trails, multiple aid and hydration stations, drop bag service, and a post-race picnic with finisher awar..

Run the trails of Croom Park at night in this unique evening event. Choose from three distances on a marked 7-mile loop. A headlamp is required to experience this nocturnal trail run.

Treat Trot-Orlando in Minneola, FL on June 6, 2026 offers in-person and virtual options across Kids Dash, 1 Mile, 5K, 10K, 15K, plus a volunteer then run option. Registrations include a shirt, bib, medal, photos, and postrace snacks.

Join the Treat Trot at Gadsden Park in Tampa for a day of running with distances ranging from a Kids Dash to a 15K. Enjoy chip timed results, finisher medals, and free event photos in a scenic park setting.

A chip timed trail run at Lake Louisa State Park on June 13 offering 4 mile and 8 mile loops, live music, throwback swag, on-course aid and post-race food and drinks in a family friendly setting.

InHouse Ultra is an indoor backyard ultra on Woodway treadmills in St Petersburg where athletes run 5 miles each hour until one person remains. The field is limited and the winner is the last runner able to complete each hourly segment.

A night trail race of *30K* in the Green Swamp West Tract near Dade City FL across varied Florida terrain with aid stations every 3 to 5 miles, a Berm drop bag zone, post race potluck options and free campground reservations.

A multi distance running event in Tampa on July 19, 2026, featuring kids dash, 1 mile, 5K, 10K, half marathon, relay, volunteer run option, and a virtual race, with shirts, medals, and chip timing for timed events.

Summer Sizzler in Tampa on 08/01/2026 features timed 5K 10K and 15K races, untimed 1 mile and kids dash, and a virtual option. The event includes chip timing, shirts and medals, free photos and finish line treats.

Experience the Withlacoochee Forest after dark in this night trail race featuring 5, 10, and 20 mile distances. Navigate single track trails under the stars with glow stick markers and a post race picnic celebration.

An 8 Hours timed trail event at Ross Prairie Trailhead in Dunnellon, FL using the Berm Loop of the Skunk Ape 100 course across sandy fire lines, pine forests and dry prairies. Loops are 6.5 Miles with self crewing and onsite camping.

A night trail half marathon in the Green Swamp West Tract near Dade City, FL, with a run and a ruck option, pink-flagged course to McNeil Trailhead, stocked aid at the turnaround, and a post race potluck and camping options.

A timed lake-lap endurance event at Lake Hollingsworth in Lakeland, FL offering 12 hour and 6 hour individual races plus a 12 hour 5-person relay. Laps are 2.84 miles and part of every entry supports the Pheel Good Foundation.

Enjoy a run or walk along the paved Pinellas Trail in Dunedin with a festive finish at HOB Brewing Company. Participants receive a medal, t-shirt, and a craft beer for those over 21.

Join this local running event in Tampa featuring distances from a Kids Dash to a Half Marathon. Enjoy chip-timed results, pacers, and finisher medals for all participants in a family-friendly atmosphere.

A point-to-point 50K on the Florida National Scenic Trail Western Connector near Ocala, Florida, with minimal course markings so runners must carry a phone and download the GPX; aid stations and one drop bag location are provided.