Trail Running calendar near Naples 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 natural beauty of Carlton Reserve at this Florida trail event. Runners can choose between three distances and enjoy a pre race stretch session with recovery snacks and awards for various age groups.

Caloosa Fest in Alva, Florida offers a Half Marathon and a 5K held on the Caloosahatchee Regional Park mountain bike trails, featuring single track, grass sections, aid stations, packet pickup options, and on-site vendors.

Single loop trail races of 50k, 25k, 5k and a Youth 5k at Carlton Preserve in Venice FL on January 30 2027, organized by RunFluent. Registration is on UltraSignup and closes January 28.

A 10.25 mile trail race in Naples on Feb 13, 2027 with a legacy entry option requiring finishes from 2022 through 2026. Includes age group awards, prize money, and free participant photos.

Experience a scenic trail race through the Carlton Reserve in Venice with distances ranging from 5k to 15k. Enjoy post race snacks and unique handmade wood awards in a festive community atmosphere.

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.

Trail races on the wooded 250 acre grounds of Gator Wilderness Camp School include 5K, 10K and 15K options, a kids dash, and a one day virtual race. Proceeds benefit the school and shirts are guaranteed for early registrants.