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 37-mile point-to-point road race from Port Mayaca to Stuart Beach, held in the South Florida heat. It includes solo and relay options and finishes with an ocean view. The event aims to raise awareness for local waterway conservation.

Event Overview The Vero Beach Octopus Ultra takes place on July 11-12, 2026, in Vero Beach, Florida. The event is based at the Environmental Learning Center (ELC), located at 255 Live Oak Dr. A portion of the proceeds from the race will be..

A 30 km night trail run through the diverse and wildlife-rich terrain of Florida's Green Swamp. The event features a supportive atmosphere with no time cut-off and a festive post-race potluck. It's part of a larger trail series and is marke..

Event Overview The Trident Trail Races is an annual trail running event held in late July at the Jupiter Ridge Natural Area in Jupiter, Florida. The event features multiple race distances with a focus on running on ancient sugar sand dunes..

Experience the Withlacoochee Forest after dark in this night trail race featuring 5, 10, and 20 mile distances. Navigate single track trails under the stars with glow stick markers and a post race picnic celebration.

The Wildcat Ultras features a friendly, loop-based course on grass and dirt paths in a Florida park. Runners can choose from five distances, enjoying frequent crew access and a fully stocked aid station. The event offers on-site camping and..

Experience the excitement of cross country racing under the lights at the world famous Apalachee Regional XC Park featuring distances from 3km to 8km for all ages and levels.

The Wild Boar Night Run is a half-marathon trail race through Florida's Green Swamp West Tract. Held at night in September, it features a stocked aid station and a festive post-race potluck party. All finishers receive a choice of a commemo..

The Osprey Trail Run takes runners through the scenic Oxbow Eco-Center preserve in Port St. Lucie. Choose from 25K and 8K running distances or an 8K walk. It's an eco-conscious, cup-less event set on boardwalks and trails along the river.

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.

Enjoy a run or walk along the paved Pinellas Trail in Dunedin with a festive finish at HOB Brewing Company. Participants receive a medal, t-shirt, and a craft beer for those over 21.

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.

Run through the scenic marshes and forests of Conservation Park to support local estuary protection. Take part in a 10K, 5K, or Fun Run on groomed trails and boardwalks during National Estuaries Week.

Experience the scenic Nocatee Greenway Trails in Ponte Vedra Beach with race distances including 10 miles, 10K, and 5K. This event features road and trail running alongside a dedicated 5K ruck and virtual race options.

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,..

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..