Trail Running calendar near Fort Myers Beach 2026-2027

Join the 26th annual Scrub Jay Races at Oscar Scherer State Park in Osprey, FL on January 24, 2026, with a fast 5K, a technical 10K trail scramble, and virtual options. Enjoy scenic courses, finisher medals, and proceeds supporting Friends..

Run the scenic Harns Marsh 5K on January 24, 2026 along marsh lined trails with wide open skies and great bird watching. All finishers get a commemorative medal and race shirt while a one mile fun run makes this a perfect family outing.

Travel through time at the Time Travel Half Marathon in Punta Gorda on Jan 24, 2026. Choose 5k, 10k, half marathon, mile or kids dash with chip timing, designer shirt, custom medal and free photos, plus a virtual option.

RunFluent's Coo Wah Chobee returns as a single loop trail run at Carlton Preserve in Venice FL, featuring mixed single and dual track trails. Distances from 50k to Youth 5k, plus signature swag and Wicked Skin awards.

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.

Run the Hero Dash 5K at Legacy Park in Venice, Florida to support Respect 1st Responders and help fund Disaster Relief Kits. Enjoy music, food trucks, vintage emergency vehicles and family fun after the race.

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.

Sasquatch invites runners to Carlton Preserve in Venice Florida for 15k, 10k, 5k and a virtual race on Feb 15 2026. Expect race shirts, snacks, live music, vendor booths and a guided group stretch for all abilities.

Run 118 miles around Lake Okeechobee on the scenic levee trail in this iconic ultramarathon. Choose crew supported or self supported solo cart divisions and tackle open, exposed terrain on the race's 20th anniversary.

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.

Run or walk through shaded woods and hammocks at Gator Wilderness Camp in Punta Gorda on April 25, 2026 with 5k, 10k, 15k, a kids dash and a virtual option. Proceeds support the residential camp school for adolescent boys and finishers enjo..

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.