Trail Running calendar near Fort Myers 2025-2026

Toxic Trail 37 is a challenging 37-mile road race held in Canal Point, Florida, running from Port Mayaca to Stuart Beach. The course highlights environmental awareness, focusing on the toxic water discharge from Lake Okeechobee into the St. Lucie River and the Atlantic Ocean.The race features a mix..

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 heading south for 18.6 miles before returning. Participants have a 10-hour t..

The FGCU XC Gobbler 5K is an annual 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 be family-friendly. Proceeds s..

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 mostly on paved and crushed shell paths with some trail sections, designed for road runners who want a taste of nature. The 10K Scramble offers..

The Coo-Wah-Chobee event, held in Venice, Florida, offers 50k, 25k, 5k, and youth 5k races on a single-loop course through Carlton Preserve. This scenic park features a mix of single-track and dual-track trails, providing a varied and engaging running experience. Organized by RunFluent, the event is..

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..

Lost 118 Ultra is a challenging 118-mile ultramarathon held annually around Lake Okeechobee, Florida, on the Herbert Hoover Levee. Scheduled for February 28, 2026, the race features a counterclockwise loop starting and finishing in Clewiston. The course offers expansive views of the lake and its wil..

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..