Trail Running calendar near Naples 2026-2027

A Halloween themed trail event in Englewood offering a 5K and a 1 mile walk at Ann & Chuck Dever Regional Park. Shirts, bibs, 5K finisher medals, costume awards and proceeds benefit 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 20K Stampede Challenge combining both events. The event includes awards, finisher hats, food, live music and supports Eirene Ranch.

The Your First Mud Run at Naples / Ave Maria (FL) will take place in Autumn Woods on Saturday 7 November 2026.

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.

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 single loop trail race at Carlton Preserve in Venice FL offering 50k, 25k, 5k and a youth 5k on January 30, 2027. RunFluent organizes the event and provides swag and awards from Wicked Skin.

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.