Trail Running calendar near Longwood 2026-2027

A 100-mile ultramarathon and a 100 furlongs (12.5 mi) event at Colt Creek State Park on January 16–17, 2027, run as six 16.8 mile loops with three staffed aid stations and loop-by-loop drop bag access.

A chip timed 5 km run and walk at Masaryk Winery in Masaryktown, Florida on January 16, 2027, with a helper registration option, race items including a t-shirt and wine glass, and results posted online by J3 Timing.

A multi-distance trail event in Christmas, Florida on January 30 and 31, 2027, running through Tosohatchee and nearby state forests with single track, varied terrain, wildlife viewing, course maps, aid station details, and crew and voluntee..

A relaxed 12 hour trail event at Whispering Pines City Park in Inverness, FL, featuring a marked 5 mile loop, an aid station potluck, and finisher awards for at least 10 miles. Capacity is 185 runners.

Trail races at Bone Valley ATV Park include a 10K, 5K, and a 1 mile color run on hilly, uneven trails. Back to back challenge options require an 18 minute per mile pace and awards are given by age category.

Trail races from Magnolia Park along the Lake Apopka shoreline offering 30K, half marathon, 8 mile, and 5K courses. The event uses hard-packed and packed lime rock trail surfaces with aid stations, technical shirts, and finisher medals.

Trail races on February 14, 2027 in Seminole State Forest at the Bear Pond Trail Head offer 5K, 12K and half marathon distances. The nonprofit event directs proceeds to forest improvements and registration fees may be tax deductible.

A coastal ultra along Florida’s Space Coast with four distance options, a beach finish, themed awards, and a 100-runner limit; all entries require a support crew.

A 15th annual 5K at Marion County Airport in Dunnellon where participants run on the airport tarmac, with medals for age group winners and a Traveling Cup for the fastest team. Proceeds support septic maintenance reimbursement grants for co..

Experience a unique single loop trail run through the Withlacoochee State Forest featuring 33 1/3 mile, half marathon, and 6K distances. Enjoy riverside trails and celebrate your finish with a post race barbecue and handcrafted medals.

A chip timed 5K run/walk at Formosa Winery in Kissimmee on March 14, 2027. Registration includes a T-shirt, a medal that doubles as a bottle opener, a pour of cider and a homemade cider donut.

The Silver Springs Half Marathon will take place in Silver Springs on Sunday 28 March 2027. You can run between 3 and 13 miles.

A team-based adventure in New Smyrna Beach where two-person teams tackle 20-plus obstacles including puzzles and physical tasks. Participants must wear the event shirt and bib; racers must be at least 10 years old.

A backyard ultra at Lake Louisa State Park on April 10, 2027 where runners complete a 4.167 mile loop each hour until they can no longer start a loop; shirts, medals, ribbon sliders, and multiple award categories are offered.

Trail races at Colt Creek State Park on April 17, 2027 offer 5K, 10K and Half Marathon routes on well-marked, runnable trails through pine forest and lakes, with chip timing, finisher medals, aid stations and post-race snacks.

Trail marathon, half marathon, and 10K on unpaved Withlacoochee State Forest trails with three aid stations and mandatory personal hydration; primitive camping is available near the course.