Trail Running calendar near Kissimmee 2026-2027

A backyard ultra in Lake Wales where runners complete repeated 4.167 mile loops each hour until one runner finishes a final solo loop and is declared the winner.

Lake Louisa State Park Trail Run on November 7, 2026 offers 5K, 10K and half marathon routes through pine forests, lakeshores and meadows. The course is chip timed, has aid stations and on course restrooms, and includes medals and post race..

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.

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.

Savage Race in Dade City Florida on November 14 2026 features a 3 plus mile course and a 5 to 7 mile course with multiple obstacles; parking is $20.

The 6th Annual Veterans Run in Tampa returns with in-person and virtual races along the Courtney Campbell Causeway, offering 5K, 10K, half marathon, and a 15.5 mile course with certified timing and aid stations.

A point-to-point 100 mile urban endurance run through Tampa Bay on November 14, 2026, organized by Skunk Ape Events. The mostly flat course passes downtown Tampa, beaches and multiple aid stations, with an overall 36.5 hour cutoff.

A well marked 5K loop on the Florida Trail in Ocala with running and rucking divisions, live timing, race day packet pickup, and a custom finisher medal; ruck entrants must meet specific weight and pack rules.

Experience the natural beauty of Lakeland at Colt Creek State Park for a trail event featuring distances from 14 miles to a 60 mile ultra. Enjoy a loop based course with handcrafted medals and a post race picnic.

A set of runs on November 21, 2026 in Brooksville, Florida features a 5K trail run, a 2.5K Turkey Trot with costumes encouraged, and a short Color Fun Run with colored powder. Proceeds support Scouting programs.

A Thanksgiving-themed 5K at Waterfront Park in Clermont, FL on November 26, 2026. The out and back course runs on the Upper Tampa Bay Trail and registration includes chip timing, a shirt, a finisher medal, awards, and photos.

A Thanksgiving 5K on the Upper Tampa Bay Trail in Tampa, FL on November 26, 2026. The chipped timed 5K includes a finisher medal, a soft short sleeve shirt, age group awards, free photos, and holiday-themed elements.

A trail ultramarathon at Lake Louisa State Park in Clermont, FL offering 50K and 25K on mostly singletrack with sandy hills and gravel, four aid stations, free race media, and finisher medals.

Trail Florida is a December team trail relay at Alafia River State Park near Tampa featuring a 126.4-mile course, multiple team formats, on-site camping in Ragnar Village, and weekend activities including a bonfire, music, glamping, and hol..

A marked 16.8 mile course preview at Colt Creek State Park in Lakeland, FL, with unstaffed water stops and primitive group camping available the night before.

RunFluent Christmas is a trail event in Lutz, FL on December 12, 2026 offering multiple distances including a new 13.1. The course uses mixed single and dual track with grass sections and includes finisher woodals and age group awards.

A sold out 5K and virtual 5K at the Florida Conservation and Technology Center in Apollo Beach supporting manatee conservation, with proceeds donated to the Florida Fish and Wildlife Conservation Commission.

Candy Cane Course in Orlando on 12/13/2026 offers 5K, 10K, 15K, a 1 Mile, a Kids Dash and a virtual option. Entries normally include a designer shirt, custom bib and finisher medal, with youth pricing for ages 12 and under.

Central Florida Spartan Trifecta Weekend at Skipper Ranch in Sebring on Dec 19 and 20, 2026 features Sprint, Super, Beast and kids races across farmland, marsh and mud.

Runs on 4.17 mile loops at Lake Wailes Park in Lake Wales FL with 12 hour, 6 hour, 4.17 mile and 12 hour relay options.