Trail Running calendar near Fort Myers Beach 2026-2027

A second annual single loop trail event at Carlton Preserve in Venice, FL offering 50k, 25k, 5k and a youth 5k. The organizer provides event swag and Wicked Skin awards and registration closes January 29, 2026.

Join the Pine Island Calusa Trail 5K on January 31, 2026 in Bokeelia, Florida for a scenic yet rugged trail run with solo, family and parent child entry options. Medals, post race refreshments and proceeds support Kiwanis youth programs.

A community 5K at Legacy Park in Venice, FL on January 31, 2026, with two age-based categories, chip timing, and post-race activities. Hosted by Respect 1st Responders to raise funds for Disaster Relief Kits; field limited to 200 runners.

Run the Ranch 5K in Sebring FL on Jan 31, 2026 invites runners and families to a scenic light trail course. Support Highlands County scholarships while racing at any pace and competing for age group medals.

Celebrate Mardi Gras at Celery Fields with 5k, 10k and canicross races for runners and their dogs. Expect shirts, post race snacks, live music, vendors and age group awards plus a guided warm up.

Trail runs at Carlton Preserve in Venice on February 15, 2026 with 15k, 10k, 5k and a virtual race. The event includes a race t shirt, post race refreshments, music and age group awards.

A 118 mile loop on the Lake Okeechobee Scenic Trail held Feb 28, 2026, with crewed and solo self‑supported cart divisions. Single halfway aid station, 18 hour halfway and 38 hour finish cutoffs, and a $118 entry fee.

Join the Kraken road race in Sarasota on April 12, 2026 for a fun 5k or 10k along scenic routes. Enjoy race shirts, snacks, a finisher bottle opener, live music, vendors and age group awards for a festive Sunday run.

Run a scenic 5K through Lovers Key State Park on April 18, finishing by the Gulf of Mexico with chances to spot dolphins, shorebirds, and turtles. Proceeds benefit Friends of Lovers Key and park admission is included with registration.

Join the Englewood Beach Turtle Trot on April 18, 2026 in Englewood, FL for a scenic sand out and back 5K or a 1 mile fun run. All finishers receive a sea turtle beach towel and a commemorative medal that doubles as a magnet.

A community 5K event on April 18, 2026 in Punta Gorda with timed and untimed 5K options, participant shirts, chip timing, trail and sidewalk course, on-site packet pickup, parking, and age group awards.

Trail races at Gator Wilderness Camp School in Punta Gorda on April 25, 2026 offering 5k, 10k, 15k, a kids dash and a one-day virtual option. Proceeds support Gator Wilderness Camp School, a 501c3 residential program.

Celebrate Halloween with the Trick or Trot 5K at Ann and Chuck Dever Regional Park on October 17, 2026, featuring a 5K trail run and 1 mile walk on scenic dirt and gravel paths. Wear your best costume for prizes, grab a shirt and medal, and..

Challenge yourself on scenic single track and rolling trails at Caloosa Fest with a 5K or Half Marathon through Caloosahatchee Regional Park. Enjoy on site vendors, gear demos, finisher medals and course support throughout the morning.