Trail Running calendar near Fort Myers 2025-2026

Trick or Trot 5K Trail Run, presented by Mazda of Port Charlotte, takes place at Ann & Chuck Dever Regional Park in Englewood, Florida. The event features a 5K trail run on a mostly dirt and gravel course, plus a 1-mile trail walk dubbed the Zoomers Trick or Trot. Participants are encouraged to wear..

The Legacy Trail Ultra is a free 60-kilometer ultramarathon held in Sarasota, Florida. In its fourth year, the event follows an out-and-back course along the Legacy Trail, starting at Payne Park and heading south about 18.6 miles before returning to the start. There are no road closings and only lim..

The 14th Annual FGCU XC Gobbler 5K is a community running event held at Florida Gulf Coast University’s Alico Arena in Fort Myers, Florida. The event features a 5K run/walk that loops around the scenic campus, a 1-mile run/walk, and a Tot Trot for children, all designed to support the FGCU Cross Cou..

The Trail Hog Half Marathon is a trail running event held at Carlton Preserve in Venice, Florida. It features three race distances: a half marathon, a 10k, and a 5k, catering to a wide range of runners. Participants enjoy a festive atmosphere with local vendor booths, music, and community spirit.The..

The Caloosa Fest 5K is a trail running event held at Caloosahatchee Regional Park in Alva, Florida. Scheduled for December 6, 2025, it is part of a day-long festival that also features ultra races of 25K and 50K distances. The event offers a scenic trail course with a supportive atmosphere including..

The Caloosa Fest Ultra in Alva, Florida, at Caloosahatchee Regional Park, offers 50K and 25K ultramarathons along with a 5K trail race. The course features an 11.1-mile loop with varying terrain, rolling hills and technical sections, running the perimeter along Green, Black and Blue trails. Runners..

The Scrub Jay Races, held annually at Oscar Scherer State Park in Osprey, Florida, feature a 5K and a challenging Scramble 10K trail run. The 5K course is road-runner friendly, mostly on asphalt, pavers, and crushed shell paths, with the final mile on park trails including a small sandy section. The..

Coo-Wah-Chobee 50k-25k-5k is a RunFluent event held at Carlton Preserve in Venice, Florida. The second annual race offers a single-loop 50k, plus 25k, 5k, and a youth 5k option, appealing to runners of varying abilities. Runners navigate a course that blends mixed single-track and dual-track trails..

The Sasquatch Run in Venice, Florida, is a vibrant trail running event held at Carlton Reserve. It offers multiple race distances including 15k, 10k, 5k, and a virtual race option, catering to a wide range of runners. Participants enjoy a festive atmosphere with local vendor booths, music, and commu..

The Lost 118 Ultra is a challenging 118-mile ultramarathon held annually around Lake Okeechobee, Florida, on the Lake Okeechobee Scenic Trail (LOST). Scheduled for February 28, 2026, this solo event requires runners to complete a full counterclockwise loop on a mostly paved 10-foot-wide asphalt path..

Kraken is a running event in Sarasota, Florida, offering 5k and 10k distances. The atmosphere blends racing with a festival vibe, featuring vendor booths and live music. Runners receive snacks, refreshments, a stylish T-shirt, and a finishers bottle opener.An awards ceremony honors the top three mal..

Set on 250 acres of Gator Wilderness Camp School grounds in Punta Gorda, Florida, the Gator Wilderness Camp Trail Run/Walk offers 5k, 10k and 15k courses through diverse woods and shaded hammocks. The event supports the camp, a 501(c)(3) residential program for at‑risk adolescent males, with race pr..

Lake to Ocean 100K is a 100-kilometer point-to-point trail race from the NENA trailhead in Port Mayaka, Florida, to Hobe Sound beach. The course is mostly single-track and remote, weaving through changing ecosystems—from ancient sand dunes with scrub oak and sand pine to pine flatwoods, palmetto, oa..