Florida
Florida Trail Running Calendar 2026-2027
Explore the best trail runs in Florida for 2026-2027! Our updated list features 186 exciting trail runs across the region. Find your next trail run in Florida below and join the trail community at these great events!
August 2026
A free, noncompetitive group 50 mile run through St. Augustine with on-route support, post-run refreshments, giveaways, and a 2027 race announcement.
Free guided trail run at Seacrest Scrub covering about 3 miles on mainly sandy natural trails through pines and scrub, with registration closed and a waiting list available.
September 2026
Looped ultramarathon at the Escambia County Equestrian Center in Pensacola featuring races from 15 miles to 100 miles on mostly grass and dirt.
Out and back ultramarathon on the Pinellas Trail in St. Petersburg covering just over 46 miles on September 5, 2026.
A charity event in Milton, FL offering a 1 Mile and an all-terrain 5K, with hydration stations, shuttle service, and half of ticket sales donated to cancer charities.
Daytona Beach Labor Day 5K offers a standard 3.1 mile race, a barefoot beach division, a virtual 5K, and a free 100 meter kids fun run with medals and awards.
A community run and walk on September 7, 2026 at JR Alford Greenway in Tallahassee supporting mental health awareness and suicide prevention. Options include a timed 5K, an untimed 5K, a 1 mile walk and event T shirts.
A two-day cross country festival in Tallahassee with nighttime collegiate, high school, middle school and open races at Apalachee Regional Park.
Memorial stair climb at the Seminole Hard Rock Guitar Hotel in Hollywood, FL on Sep 11, 2026 with 110 story, 72 story and 36 story climbs benefiting veteran and firefighter causes.
A trail half marathon and ruck through Green Swamp West Tract near Dade City with an out and back Florida Trail route and staffed aid at the turnaround.
Trail event in Jupiter FL with 50K, a 12 hour loop format and an untimed fun run around 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.
S.O.S. in Middleburg, FL on September 12, 2026 is a loop event offering a 9K and 3, 6 and 12 hour timeframes on the Sandridge Trail with stocked aid stations.
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 neon-lit night cross-country event at Bennett Park offering 2-mile and 4-mile courses with required headlamp and a referral refund program.
Summer Sizzler at Gadsden Park on September 13 2026 offers races from a kids dash to 15K plus a virtual option, with shirts, finisher medals, timing, and finish-line treats.
Looped trail race at the Oxbow Eco Center in Port St. Lucie on Sept 19, 2026 with 8k and 25k options; proceeds support local environmental education.
Timed lake-lap ultrarun in Lakeland, FL offering 12 hour, 6 hour and 5 person relay formats on 2.84 mile laps with a 200 runner cap and proceeds to the Pheel Good Foundation.