Florida
Florida Trail Running Calendar 2026-2027
Explore the best trail runs in Florida for 2026-2027! Our updated list features 203 exciting trail runs across the region. Find your next trail run in Florida below and join the trail community at these great events!
October 2026
A Halloween-themed 5K, 1-Mile Fun Run and virtual 5K in Dunedin/Palm Harbor benefiting Club-214 Land & Sea and veteran support services.
A community 5K at DeLeon Springs State Park on October 17, 2026, offering an in-person run and a virtual 5K to support the Friends of DeLeon Springs State Park.
An urban 5K adventure race and a shorter untimed fun run at Independence Landing in Tallahassee on October 17, 2026. The 5K features at least five challenges along the route and finishers receive medals.
Second annual Withlacoochee River 5K Run/Walk in Dade City on Oct 17 2026 with live 5K, 1 mile and virtual 5K plus medals, awards and charitable giving.
A Florida-based series of off-road endurance events featuring recurring 5K and 10K trail runs, cross country races, and longer mountain-bike competitions.
Trail and ruck events of 5 and 10 miles at Jennings State Forest on October 18, 2026, featuring the Sawyer Trail, Many Seeps Bridge, cupless aid station, and awards.
A USATF sanctioned 24 hour event at Gulf Coast State College where participants run one mile every 30 minutes, with individual and two person relay options.
Experience the rolling hills and single track trails of San Felasco Hammock Preserve State Park in Alachua Florida with 25K and 50K trail races.
A Halloween-themed trail event on October 24, 2026 in Ocala with 5K and 10K run and ruck options plus challenge entries.
The 14th Annual Gopher Weedon 8K Trail Run on October 24, 2026 follows 8 kilometers of dirt and boardwalk trails through Weedon Island Preserve, with professional timing, refreshments and proceeds benefiting Friends of Weedon Island.
An evening 5K in Sebastian with a haunted trail and family activities; proceeds support counseling and peer support for local first responders.
A sixth annual 5K trail race at Jonathan Dickinson State Park with in-person and virtual options, chip timing, age-group awards, and included shirt, medal, park fee and refreshments.
Community 5K trail run in Englewood on October 24, 2026 benefiting Dollars for Mammograms and the Englewood YMCA, with a kids fun run, awards, and post-race activities.
An off road Halloween 5K at Waldo MX with obstacles, infected zones, and flag football style life flags to protect; open to ages 8 and up.
A Halloween themed trail marathon and half marathon in Ocala on October 24, 2026, run mostly on dirt trails from Baseline Trailhead Park with marked aid stations and finisher medals.
Trick or Trot 5K Trail Run in Palm City on 10/24/2026 follows unpaved two track dirt and grass trails through the Kiplinger Conservancy and includes awards, swag and hydration.
A free three mile trail run led by county biologists through the sandy scrub of Juno Dunes, meeting at Bert Winters Park in Juno Beach.
Experience a scenic single track trail race through shaded hammocks and along the Atlantic Ocean with 50k, 24k, and 12k distances in Palm Coast.
Experience the famous clay trails of Clermont in this hilly off road event featuring timed 15K and 5K distances. Run along scenic 5 Mile Road and enjoy a professional racing environment with full course support and finisher medals.