Trail Running calendar near Fort Myers 2025-2026

The Legacy Trail Ultra is a free 60K ultramarathon held annually in Sarasota, Florida, organized by the Manasota Track Club. The race features an out-and-back course along the scenic Legacy Trail, starting at Payne Park and extending 18.6 miles south before returning. Participants navigate a mostly..

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, held at Caloosahatchee Regional Park in Alva, Florida, features challenging 50K and 25K trail races on December 6, 2025. The course consists of an 11.1-mile loop with varied terrain, including rolling hills, technical sections, and scenic views along Green, Black, and Blue tr..

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..

The Coo-Wah-Chobee 50k is an annual trail running event held at Carlton Preserve in Venice, Florida. Featuring distances of 50k, 25k, 5k, and a youth 5k, the race offers a single-loop course that combines mixed single-track and dual-track trails through scenic park terrain. Organized by RunFluent, t..

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..

The Kraken is a running event held in Sarasota, Florida, featuring 5k and 10k race options. Participants enjoy a vibrant atmosphere with live music and vendor booths, enhancing the race day experience. Each runner receives snacks, refreshments, a stylish t-shirt, and a finisher's bottle opener.The e..

The Gator Wilderness Camp Trail Run/Walk is a scenic event held at Gator Wilderness Camp School in Punta Gorda, Florida, featuring 5k, 10k, and 15k trail races through diverse woods and shaded hammocks on 250 acres. The event supports a residential school for struggling adolescent males. Runners can..

The Lake to Ocean 100K is a scenic point-to-point ultramarathon held in Florida, starting at the NENA trailhead in Port Mayaka and finishing at Hobe Sound beach. Recognized by Outside online as one of the top 10 most beautiful trails worldwide, the course features mostly single-track remote trails t..