Florida
Florida Trail Running Calendar 2026-2027
Explore the best trail runs in Florida for 2026-2027! Our updated list features 209 exciting trail runs across the region. Find your next trail run in Florida below and join the trail community at these great events!
September 2026
A community 5K/10K/15K on the Pinellas Trail in downtown Dunedin at HOB Brewing Company on September 27, 2026, with electronic timing, finisher medals and a post-race party including one free draft beer for participants 21 and over. The event support..
A trail 5K and virtual 5K at Wickham Park with finisher medals, age-group and team awards, packet pickup at Running Zone, and proceeds benefiting Florida Wildlife Hospital.
Cross country 5K and 10K at Amelia Earhart Park in Hialeah, with asphalt, grass and dirt sections; kids under 15 run free and a waiver is required.
October 2026
The John Holmes Trail Run takes place at Croom Park and Withlacoochee State Forest on October 3, 2026, offering 50K, 16 mile and 9 mile options. The field is limited to 250 runners and this is the event's 34th running.
A multi-distance running event in Jacksonville featuring timed endurance formats and several 5k options on a tree lined asphalt loop, with proceeds supporting the Shelter for Elders initiative through Jacksonville Area Legal Aid.
A timed tower climb at Tampa City Center to the 41st floor with 861 steps, bailout floors, water stations, event t shirt, finisher medal, and awards across categories.
Seventh annual Florida Running Club cross country meet on October 3, 2026 at West End Community Park in Newberry, FL with men's and women's 5 km races.
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.
Obstacle course weekend at Lake Nona in Orlando featuring a 5 km Sprint, 10 km Super, kids races, workshops and a 4 hour Hurricane Heat.
A trail event at Tall Timbers on October 10, 2026, offering a 20K run and a 14K ruck with a three hour cutoff and marked aid stations.
A community cross country 5K at Anthony Pleasant Park on October 10, 2026 with age-group medals and awards presented by the Century Lions Club.
Beachside community event at Coquina Beach offering a timed 5K, a 1 km fun run, and a virtual 5K with shirt and medal.
Trail 5K and 1 mile walk at Ann and Chuck Dever Regional Park with costume awards, finisher medals, post race refreshments, and proceeds to a local scholarship fund.
Point to point 50K on October 17, 2026 along the Florida National Scenic Trail west corridor, requiring GPX navigation and a carried phone.
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.