Trail Running calendar near Winding Cypress 2026-2027

A trail event in Naples, FL on 07/11/2026 with an eight hour time limit to complete as many two mile loops as desired. A fully stocked aid station will operate for the event and parking is on Sabal Palm Road.

A Halloween themed trail event in Englewood on October 17, 2026 featuring a 5K run and a 1 mile walk, costume awards, finisher medals, post-race refreshments, and proceeds supporting the Zoomers Scholarship Fund.

Buddy the Bull Stampede in Arcadia FL on 11/07/2026 features a 5K trail run, a 15K mountain bike race and a combined Stampede Challenge, with post-race food, finisher hats, activities for families, and support for Eirene Ranch.

A family oriented mud run in Ave Maria with 1.5 to 2 mile courses and 10 to 16 obstacles designed for adults and children. Participants five years and older can register and a dog option is available with a paid adult.

Experience the rugged beauty of Alva at Caloosa Fest featuring a half marathon and 5K trail race. Runners navigate scenic single track trails and rolling terrain through the Caloosahatchee Regional Park mountain bike system.

A family-friendly 5K featuring eleven inflatable obstacles over two laps, welcoming walkers, joggers and runners. The touring event includes a Naples stop at Naples Classical Academy on February 27, 2027; tickets are listed as on sale soon.

A road race around the Everglades' Shark Valley loop hosted by the Miccosukee Tribe, offering 5 km, 16.5-mile and 50 km distances on pavement with aid stations, on-course support, finisher medals and family activities.