Trail Running calendar near Southwest 2026-2027

Run the IQ Fiber Winter Beach Run on Jacksonville Beach with 10 mile and 5K options along firm sand at low tide on an out and back course. All runners get a long sleeve moisture wicking shirt and finishers receive medals plus hot chocolate.

Run the Florida Roots Trail Series at Fort Clinch Park on January 24 on scenic single track trails that circle the historic fort. Choose 10K, 30K or 50K and enjoy real food, finisher shirts and post race meals and beer.

Run the rugged 8k at Moccasin Creek Off Road Park on Jan 24, featuring roots, mud and open fields with chip timing and finish photos. Proceeds support Hooves To Freedom equine therapy and entry includes a long sleeve tech shirt.

This Ain't Your Mothers 50K and Trail Marathon on January 25, 2026 in Middleburg Florida offers single track, waterfalls, stream crossings and scenic vistas on the Pioneer Trail. Choices from 7K to 50K suit racers and adventurers.

Dark Anchor is a timed ultramarathon on Jekyll Island with a fast, flat 3 mile loop run counterclockwise over a 34 hour format. Distances from 25K to 100 miles promise a supported, community driven challenge; 2026 is sold out.

Experience the Sombrero Ultra Running Festival in Middleburg FL with races from 3 to 48 hours, live music, vendors, and themed giveaways. Bring your crew and enjoy a runner village, a single aid station, medical support, and awards.

Celebrate the Angry Tortoise's 13th anniversary at Cary State Forest on Feb 21 2026 with flat, fast trail courses in 25K and 50K. Well supported aid stations, post race lunch, and scenic forest roads make for a fun day.

Experience single track trails at the Swamp Trail Race in Palm Coast, Florida on Feb 21, 2026, with distances from the breast cancer fundraiser Debby 10K to a tough 50K and a new 50K relay. A small field creates an intimate, friendly race v..

Join the Painted Horse Urban Ultra in Ocala on Feb 21 for a self supported, navigation heavy adventure. Choose 55k or 25k routes that visit dozens of painted horse sculptures, and it is not a race but a sightseeing scavenger hunt.

Join the family friendly Run for the Springs 5K through scenic Silver Springs State Park trails on Saturday Feb 28, 2026. Enjoy a kids area, refreshments, door prizes, age group medals and a Traveling Cup for the fastest team.

Challenge yourself at the Jacksonville Trail Experience at Diamond D Ranch, an early season Spartan Trail that blends fast, runnable sections with muddy, ankle biting terrain. Choose 10K or 21K to test speed and grit.

Two Prairies Ultra is a low key FAT ASS on the Florida Trail near Salt Springs, FL, with 50K and 30K options through scenic Juniper and Hopkins Prairies. Limited to 50 runners and encourages a trail donation; register by March 7.

Bring your pup and hit the sand for Run with the Pack, a dog friendly 5k and 1 mile fun run at Jacksonville Beach Pier. Enjoy beachside routes, a shirt and medal, and a post run party while supporting Fur Sisters Furever Urs Rescue.

Lace up for the FTC Archer Braid Trail 5k & 10k in Archer, Florida, a flat, paved out and back through peaceful countryside. Choose 5k or 10k, enjoy timed results, age group awards, and a midcourse hydration stop.

Hit the trails at Paynes Prairie Preserve on March 28, 2026 for the Trail of Payne featuring 5k, 10k and a 1 mile fun run. New course winds through varied terrain from soft sand and roots to sunny prairies and shady forest.

Explore the scenic trails of Silver Springs State Park on March 29, 2026 with a half marathon, 10K, 5K or virtual trail run. Enjoy a custom tech shirt and finisher medal as you race past springs, river and abundant wildlife.

Join the Safe Animal Shelter Fundraiser Trail Run in Middleburg Florida for scenic miles on the Sandridge Trail while helping local pets in need. Choose from a half marathon, 10K or 5K on wide flat trails, enjoy swag and a raffle entry.

The Skunk Ape Trail Race in Ocala, Florida offers 50 Mile and 100 Mile ultramarathons on a scenic 50 mile out and back loop through pine scrubs, lakes and prairie. Enjoy rugged trails, strong aid support and memorable finisher swag.

Run the Free to Fly Trail 5K at San Felasco Hammock Preserve on April 25, a scenic trail race that raises funds for Anew and survivors of human trafficking. Enjoy nature and make a real impact through housing, counseling and vocational supp..

Run laps on a shaded flat one mile loop between river and ocean at the River to Sea 12 6 Hour Trail Race in Palm Coast FL on Aug 1. Choose 12 hour or 6 hour timed options with a fully stocked aid station and friendly volunteers.