Trail Running Calendar Florida 2026-2027

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.

A timed lake-lap endurance event at Lake Hollingsworth in Lakeland, FL offering 12 hour and 6 hour individual races plus a 12 hour 5-person relay. Laps are 2.84 miles and part of every entry supports the Pheel Good Foundation.

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.

Join this local running event in Tampa featuring distances from a Kids Dash to a Half Marathon. Enjoy chip-timed results, pacers, and finisher medals for all participants in a family-friendly atmosphere.

A multi-distance running event at Jay Blanchard Park on September 27, 2026 offering a half marathon, 10K, 5K, 1 mile, kids dash, volunteer option and a virtual race, with bibs, shirts and finisher medals provided for most entries.

Trail races on the Croom Hiking Trail in Brooksville, Florida offering 50K, 16 mile and 9 mile options plus a spectator entry. The route passes longleaf pines, scrub oak hills, creek bottoms and cypress ponds.

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.

Orlando Spartan Weekend at Lake Nona on Oct 10 and 11, 2026 features obstacle course events from a 5 km sprint with 20 obstacles to a 10 km super with 25 obstacles. Team entries can secure shared start times and verified discounts are avail..

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 Western Connector near Ocala, Florida, with minimal course markings so runners must carry a phone and download the GPX; aid stations and one drop bag location are provided.

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,..

An urban 5K adventure race in Tallahassee with at least five on course challenges and finisher medals. A separate untimed fun run under one mile is offered and T shirts are available for an extra $10.

A USATF sanctioned 24 hour event at Gulf Coast State College where participants run one mile every 30 minutes. Individual and two person relay options, age minimum 16, with shirt and finisher medal for registered runners.

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.

Trail races of 25K and 50K through San Felasco Hammock Preserve near Alachua, FL, featuring single-track, double-track and rolling terrain; aid stations supply water and snacks but no cups or gels. Proceeds support Friends of San Felasco.

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.

An 8K trail race through Weedon Island Preserve on October 24, 2026, featuring natural trails, boardwalks, views of Tampa Bay and professionally timed results; proceeds support Friends of Weedon Island.

A trail event in Palm Coast Florida featuring 50K, 24K and 12K loops on mostly single track near the Atlantic Ocean. The field is limited to 125 runners and all finishers receive shirts and awards.