Trail Running Calendar Florida 2026-2027

The Independence Double offers a no-frills running experience over two days in Winter Park, Florida. Choose from five distances each day on a flat, shaded loop course. Expect a casual, hand-timed event with a focus on community and low entr..

A point to point road race in Canal Point, Florida, running about 37 miles to Stuart Beach. The event highlights Lake Okeechobee discharge impacts and offers solo and relay options with regular aid stations and a shuttle option.

The Vero Beach Octopus Ultra uses eight out and back arms from a central base at the Environmental Learning Center, offering distances from a 5K to 100 miles. A 32 hour limit applies and crews are strongly recommended.

A night trail running event on July 18, 2026 in Green Swamp West Tract near Dade City, FL, covering 30K of varied Florida terrain with aid stations every 3 to 5 miles, finisher glassware, event stickers, and a post race potluck.

Timed running and rucking on a flat 1.25 mile paved loop at the former Cecil Field in Jacksonville, Florida. Events run for 3, 6, 9, or 12 hours with a 6 hour relay option, on-course aid, and a custom finish medal.

The The Trident will take place in Jupiter on Saturday 25 July 2026. You can run between 13 and 102 miles.

A flat, shaded trail loop in Palm Coast, Florida hosts timed 6 hour and 12 hour events beside the river and ocean. The race includes a fully stocked aid station and is organized by an experienced race director.

A night trail event at Holder Mine Campground in the Withlacoochee Forest offering 5, 10 and 20 mile single-track courses. Headlamps are required and courses are marked with reflective pins and glow sticks.

Wildcat Ultras is a loop based ultramarathon at the Escambia County Equestrian Center in Pensacola offering 100, 100K, 50, 50K and 15 mile distances with chip timing, a centrally located aid station, and RV parking.

A trail event at the Oxbow Eco-Center in Port St. Lucie on Sep 19, 2026, offering 25K, 8K and an 8k walk. The race is cup-less so participants must bring their own water carry system.

Miami 100 is an open road 100 mile ultramarathon through Miami neighborhoods with progressive course directions and checkpoints. The field is limited to 50 runners and an optional 130 mile challenge adds 30 miles after the main race.

Run the Dunedin Oktoberfest 5K or 10K along the scenic Pinellas Trail, finishing at HOB Brewing for postrace Oktoberfest vibes. Stroller and dog friendly with a beer armband for 21 and over and finisher shirt and medal.

A community 5K, 10K and one mile event along the LaVilla Link and S Line Rail Trail in Jacksonville. Proceeds support Groundwork Jacksonville and local creek restoration and trail-building efforts.

A multi-distance running weekend in Ponte Vedra Beach with in-person and virtual 10 mile, 10K and 5K options, a course on Nocatee Greenway trails, branded gear and awards for overall and age group finishers.

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..

A point to point 50K on the Florida National Scenic Trail in Ocala, where runners navigate by orange blazes, must download the GPX and carry a phone, and can use on course aid and one drop bag location.

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,..

This dog-friendly 5k trail run takes place off-road at Rock Springs Run State Reserve in Sorrento, Florida. Registration includes entry for a runner, their dog, and a guest, with proceeds supporting animal-focused causes. The event features..

Trail running event at San Felasco Hammock Preserve near Alachua, FL, offering 25K and 50K circuits on single track, double track and fields. The race supports Friends of San Felasco and includes aid stations and finisher awards.

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.