Trail Running calendar near Osteen 2025-2026

The Real Florida 5K and 10K is an annual cross-country race held at Wekiwa Springs State Park in Apopka, Florida. Celebrating its 39th edition in 2026, the event features an off-road course through scenic natural surroundings. Participants receive a commemorative T-shirt and medal, with awards for o..

All Day at Holloway is a running event held at Holloway Park in Lakeland, Florida, featuring distances of 10k, 30k, and 50k, including a 5-person relay where each member runs a 10k loop. The course is a top-tier cross country route, known for being extremely well-groomed, fast, and partly used for N..

The Long Play Trail Run, held in Brooksville, Florida, offers a scenic single-loop trail race through the Croom Tract of the Withlacoochee State Forest. Participants can choose from a challenging 33.3-mile ultra, a half marathon, or a 6K, all starting and finishing at the Ridge Manor Trailhead. The..

The Two Prairies Ultra is a unique, no-fee ultra running event held in Fort McCoy, Florida, within the Ocala National Forest. Participants can choose between a 50K and a 30K distance, with the 30K covering the southern half of the course. The race starts at Pat's Island Trailhead and features two ou..

The Colt Creek State Park Trail Run, hosted by The Florida Run, takes place in scenic Colt Creek State Park, Florida. Offering 5K, 10K, and half-marathon distances, the event features well-maintained trails through lush pine forests, serene lakeshores, and open meadows. Runners experience diverse te..

The Withlacoochee Trail Marathon is a trail running event held near Lecanto, Florida, within the Two Mile Prairie Tract of the Withlacoochee Forest. Scheduled for April 19, 2026, it offers three race distances: a full marathon consisting of two 13.1-mile loops, a half marathon with one 13.1-mile loo..

The Tick is a challenging 57.41-mile ultra running event held in Alexander Springs, Florida, traversing the rugged wilderness of Ocala National Forest. The point-to-point course follows the Florida National Scenic Trail from Alexander Springs State Park to Rodman Reservoir Dam, showcasing diverse ec..

The Stomp Out Suicide Trail Race is a scenic and shaded trail running event held at Withlacoochee River Park in Dade City, Florida. Scheduled for May 9, 2026, it offers three distances: a 10K trail run consisting of two loops, a 5K trail run/walk with one loop on non-paved hiking trails, and a 1-mil..

Sweat, Swat ‘n Swear is a challenging trail running event held at Holder Mine Campground in Inverness, Florida, within the scenic Citrus Tract of the Withlacoochee State Forest. Scheduled for May 24, 2026, the race offers three single-loop distances: 50K, 25K, and 10 miles, catering to various skill..