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!
September 2026
Two day cross country festival at Apalachee Regional Park in Tallahassee with collegiate, high school, middle school and open heats held under the lights.
Join a memorial stair climb at the Hard Rock Guitar Hotel in Hollywood Florida with options for a 110, 72, or 36 story ascent to honor first responders.
A night trail event in Green Swamp near Dade City offering a half-marathon and a ruck option, marked trail, aid station at the turnaround, awards, and a post-race potluck.
Experience a low-key ultra marathon along the Loxahatchee River in Jupiter, featuring 12-hour, 50K, and Fun Run options through the scenic Riverbend Park.
A trailfest near Watercolor, Florida offering 5K, 10K and 10 Mile options on marked forest trails; proceeds support Operation Outdoor Freedom and all finishers receive shirts and medals.
Experience the Sandridge Trail in Middleburg at S.O.S., featuring a 2.75 mile loop with 9K distance options and timed events ranging from 3 to 12 hours.
Back to School Bash in Eustis is a trail run at Central Florida Bible Camp with a 1.6 mile loop, ten field day stations, and three divisions.
Two loop trail races at San Felasco Hammock Preserve State Park on September 12, 2026, with 3.8-mile and 8.3-mile courses. There are awards, post-race snacks, a $20 entry fee, and park parking fees.
A September remembrance event in West Palm Beach featuring a 110-story stair climb, a 5K fun run, a CrossFit team competition, and fundraising for POST and Operation 300.
A neon-lit night cross-country event at Bennett Park offering 2-mile and 4-mile courses with required headlamp and a referral refund program.
Trail races of 25K, 8K and an 8K walk at Oxbow Eco Center in Port St. Lucie with on site packet pickup and donations collected for local causes.
A community 5K along Jacksonville Beach on September 19, 2026, benefiting the Betty Griffin Center with timed chips, race shirts, finisher medals, vendors, and postrace Pilates.
A free scavenger hunt run from 1st Place Sports San Marco with New Balance shoe demos, teams of 4 to 5, photo clue stops, post-run breakfast and prizes.
A 100 mile open road urban ultramarathon through Miami neighborhoods on September 26, 2026, limited to 50 runners and relying on crew support, checkpoints and directional cards. A 30 mile Miami 130 Challenge is available after the 100 miles.
Complete as many 2.84 mile laps as possible around Lake Hollingsworth in this 6 hour or 12 hour endurance challenge featuring a full hot food menu.
Third annual trail run in Conservation Park Panama City Beach on September 26, 2026 supporting the St. Andrew and St. Joseph Bays Estuary Program.
YMCA Camp Winona MudFest is a 3 mile obstacle course race on September 26, 2026 in De Leon Springs, FL with more than 17 obstacles.
A 5K and 1 Mile at J.R. Alford Greenway in Tallahassee featuring single-track trails, steep final hills, and a post-race dress-alike contest.
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 5K at Wickham Park in Melbourne with in-person and virtual options, finisher medals, age-group and team awards, and proceeds benefiting Florida Wildlife Hospital.