Trail Running calendar near Kissimmee 2026-2027

Candy Cane Course in Orlando on 12/13/2026 offers 5K, 10K, 15K, a 1 Mile, a Kids Dash and a virtual option. Entries normally include a designer shirt, custom bib and finisher medal, with youth pricing for ages 12 and under.

Central Florida Spartan Trifecta Weekend at Skipper Ranch in Sebring features obstacle races across farmland, marsh and mud. Distances include Sprint 5 km, Super 10 km, Beast 21 km and a kids race, with an obstacle workshop the day before.

A looped event at Lake Wailes offering 4.17 mile, 6 hour, 12 hour and 12 hour relay options. Food is available at the Runners Village and all participants receive a long sleeve shirt.

Holiday-themed races at Gadsden Park in Tampa on December 27, 2026, with distances from a kids 50 m dash to 15K, plus a virtual option, chip-timing, shirts, medals, photos, and finish-line treats.

A looped trail event at Colt Creek State Park near Lakeland, FL, offering a 100-mile Western States qualifier and a 12.5-mile 100 Furlongs option with staffed aid stations and 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 free, donation-supported 12-hour trail event at Whispering Pines City Park in Inverness, FL. Runners use a marked 5-mile loop on mixed trails, with an aid station and a finisher award for 10 miles or more.

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 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 limited-field ultramarathon on Florida’s Space Coast offering a 100 mile race, a three person 100 mile relay, a 50 mile and a 33.3 mile point-to-point course. All events are support crew only and finish on the beach with a finisher's buck..

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.

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 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.

An obstacle 5 km through Raymond James Stadium with 20 obstacles running past the pirate ship and stadium bleachers. The weekend also includes a kids race and spectator options, with team entries and an available service member discount.