Trail Running calendar near Osteen 2026-2027

A shaded trail run and walk at Withlacoochee River Park offering 10K, 5K and 1 Mile distances; proceeds support mental health education and the PAIR Program, with limited race-day registration for the 5K and 1 Mile only.

On May 2, 2026 the TOUGH Gator 5K Mud Run offers timed 5K and 2K courses across 200+ acres of Florida wilderness with multiple muddy obstacles. All proceeds support international aid including disaster relief and school supplies.

The inaugural Moss Islesly 5K Run/Walk at Moss Park in Orlando takes place on May 4, 2026. The evening event features a Star Wars costume contest, guaranteed T-shirt and medal for early registrants, and a mixed surface course.

A remote, point-to-point 57.41-mile trail ultra on the Florida National Scenic Trail through Ocala National Forest. Crew support and a communication device are mandatory; participation is capped at 50 with a suggested donation to support th..

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.

Turkey Creek 5K Trail Run takes place May 23, 2026 in Palm Bay at Turkey Creek Sanctuary. The event offers an on-site 5K and a virtual 5K with race shirts, medals for the first 300 registrants, finish-line refreshments and age-group awards.

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.

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.

The Independence Double offers a no-frills running experience over two days in Winter Park, Florida. Choose from five distances each day on a flat, shaded loop course. Expect a casual, hand-timed event with a focus on community and low entr..

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 Orlando on 2026-07-18 featuring a half marathon, 10K, 5K, shorter youth races, relay and a virtual option with mailed packets and race swag.

A flat, shaded almost one mile loop through palm and oak hammock in Palm Coast, FL, offered as 12 hour and 6 hour timed races with a fully stocked aid station. Registrations are non refundable and close July 29.

Summer Sizzler in Orlando on 08/02/2026 features 1 mile, kids dash, 5k, 10k, 15k, virtual options, and a volunteer then run choice. Registrations include event shirts and finisher medals and select distances use chip timing.

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.

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.

A multi-distance running event at Jay Blanchard Park on September 27, 2026 offering a half marathon, 10K, 5K, 1 mile, kids dash, volunteer option and a virtual race, with bibs, shirts and finisher medals provided for most entries.

Trail races on the Croom Hiking Trail in Brooksville, Florida offering 50K, 16 mile and 9 mile options plus a spectator entry. The route passes longleaf pines, scrub oak hills, creek bottoms and cypress ponds.