Trail Running calendar near Fort Myers 2025-2026

The Day Before Mother's Day 5K is a vibrant running event taking place on Fort Myers Beach, Florida, on May 10, 2025. Participants can choose from a live 5K run/walk, a virtual 5K, or an untimed 1-mile fun run/walk. The event aims to promote community engagement and wellness, with a portion of the p..

The Lake to Ocean 100K is a premier trail running event taking place in Florida, recognized as one of the world's top beautiful trails by Outside online. This point-to-point race spans from the NENA trailhead in Port Mayaka to Hobe Sound beach, showcasing diverse ecosystems including ancient sand du..

Toxic Trail 37 is a challenging road race taking place in Canal Point, Florida, covering approximately 37 miles from Port Mayaca to Stuart Beach. This event aims to raise awareness about the environmental issues related to the discharge of toxic water from Lake Okeechobee into local waterways. Parti..

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..

Caloosa Fest Ultra is an exciting annual running event held at Caloosahatchee Regional Park in Alva, Florida. The event features a 50K ultra marathon and a 25K race, both set on a scenic 11.1-mile loop that includes diverse terrain, beautiful views, and technical stretches. Participants can enjoy ai..

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 Coo-Wah-Chobee 50k, 25k, and 5k is an annual trail running event held at Carlton Preserve in Venice, Florida. Organized by RunFluent, the race features a single-loop course with a mix of single and dual-track trails, offering challenging and scenic routes for participants. The event includes opt..