Florida
Florida Trail Running Calendar 2026-2027
Explore the best trail runs in Florida for 2026-2027! Our updated list features 167 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 beachside running event in Jacksonville Beach offering 5 mile, 5K and 1-mile races with medals, awards, food, and live music.
8 Hours of Berm is an 8 hour timed ruck at Ross Prairie Trailhead in Dunnellon FL featuring 6.5 mile loops across sandy berms and a dedicated rucking division.
Trail cross country races at Elinor Klapp-Phipps Park offering 8K, 5K and 3K distances with youth free entries and adult fee of twenty dollars. Participants are asked to bring two to four canned food items for local donation.
A free, non-competitive 50-mile group run through St. Augustine on Aug 22, 2026, with flexible distances, coaching support, post-run refreshments, and event giveaways.
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.
A 46 mile ultramarathon on the Pinellas Trail from St. Petersburg to Tarpon Springs and returning to Dunedin 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.
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 at Apalachee Regional XC Park in Tallahassee with nighttime collegiate, high school, middle school, and open heats, multiple distances, and team amenities including a coaches’ box and reserved areas.
A 9/11 memorial stair climb at the Seminole Hard Rock Guitar Hotel in Hollywood, Florida on September 11, 2026. Three climb options for firefighters and civilians, raising funds for the Wounded Veterans Relief Fund and Firefighters Benevolent of Davi..
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.
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.
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.