Trail Running calendar near Fort Myers 2025-2026

The Lake to Ocean 100K is a sold-out, 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 trail..

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, sponsored by the Manasota Track Club. The race follows 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 ti..

The Caloosa Fest 5K is an exciting running event taking place in Alva, Florida, featuring a scenic trail run. Scheduled for December 6, 2025, this festival includes not only the 5K race but also ultra races of 25K and 50K, along with adventure races. Participants can enjoy various activities, includ..

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 stretches, and scenic views along Green, Black, and Blue t..

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 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 and offers r..