Trail Running Calendar Florida 2026-2027

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..

The Itch is a rugged, point-to-point 50K trail race on the Florida National Scenic Trail. Runners navigate using orange blazes and must carry a phone with the course GPX. This no-frills event offers aid stations and a drop bag point in the..

Hit the Pinellas Trail for a Halloween-themed run supporting veterans. The Camo & Cobwebs event offers a timed 5K and an untimed 1 Mile Fun Run/Walk, both starting and finishing at de Bine Brewing Company. Expect costumes, finisher medals,..

The Commodore 24 Hour Challenge dares runners to cover one mile every half hour for a full day. You can tackle it solo or with a partner in the relay at Gulf Coast State College. All participants get a shirt and medal, with awards for top f..

Experience an off-road 5k trail run with your dog at Rock Springs Run State Reserve. This dog-friendly event features a spooky theme, finishers medals for both humans and pets, and supports local animal rescues.

The Gate2Gate Trail Run explores the diverse trails of San Felasco Hammock Preserve in Florida. Runners can choose between a 25K single loop or a 50K double loop on a course open for 8 hours. It's a benefit event supporting park friends, fe..

This Halloween trail race offers a spooky evening on the Florida Greenway. Choose from 5k, 10k, or a combined challenge in either run or ruck divisions. Costumes are encouraged, and all finishers get a medal.

Run the shaded, single-track trails of the Mala Compra Greenway, just steps from the Atlantic Ocean in Palm Coast. Choose from 50K, 24K, or 12K distances on this looped course. All finishers get an award, and free kids' races are also part..

Celebrate Halloween with a spooky 5K in Clermont. The evening event features haunted zones, a costume contest, and a live DJ. A virtual 5K option is also available.

Experience the natural beauty of the Florida Trail with point to point races finishing at Stephen Foster Folk Culture Center State Park. Support trail conservation while running through diverse northern Florida landscapes.

Experience the natural beauty of Florida at Lake Louisa State Park with trail races across rolling sandhills and shaded oak hammocks. Choose from three distances featuring scenic lakeside views and diverse forest terrain.

Experience a unique 10 mile night trail run through the forests of Jonathan Dickinson State Park. Navigate sand and dirt trails by headlamp and enjoy a festive Halloween atmosphere featuring a costume contest and post race celebration.

Experience an adventure race or trail run through the scenic landscapes of Jonathan Dickinson State Park. Choose from multiple distances and disciplines including trekking, mountain biking, and paddling in this multi sport challenge.

A community 5K at Vista View Park in Fort Lauderdale on November 7, 2026. Hosted by the Life Alliance Organ Recovery Agency, the evening run raises awareness for organ and tissue donation while honoring donors and recipients.

Celebrate Thanksgiving with a series of themed races including a Half Marathon, 10k, and 5k in Orlando. Enjoy chip timed results, finisher medals, and family friendly distances like the Kids Dash and 1 Mile fun run.

Experience the diverse trails of Dunns Creek State Park in Florida with distances ranging from 8K to 100 miles. Tackle a scenic looped course featuring pine forests and wide terrain with both running and rucking divisions available.

Join this patriotic honor run on the scenic Pinellas Trail to celebrate military veterans. Choose from 10K, 5K, or Kids Dash distances in a stroller friendly environment at Dunedin.

Celebrate Thanksgiving with this family friendly event in Tampa featuring distances from a Kids Dash to a Half Marathon. Enjoy chip timed results, finisher medals, and festive treats at the finish line.

Experience a 200 mile point to point journey across the state of Florida. This endurance trail run traverses the Florida Trail, Ocala National Forest, and coastal paths from Yankeetown to the Atlantic shores of St. Augustine Beach.

Experience an obstacle course event in Dade City Florida featuring 3.5 mile and 6.2 mile distances. Choose between competitive pro waves, open divisions, or a ruck category for a unique outdoor adventure.