Trail Running calendar near Middleburg 2026-2027

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.

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.

Discover Manatee Springs on Saturday Feb 21, 2026 with scenic trail races through springs fringed by cypress where you might spot manatees. Choose a half marathon, 10K or 5K and enjoy nature, but entries are limited so sign up early.

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 Unicorns Among Us 5k in Ormond Beach on Feb 21, in person at Ormond Brewing Company or virtually. Enjoy a chip timed 5k with event shirt and medal, a free brewery pour with your bib, and support The Heterotaxy Connection.

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.

A family-oriented 5K trail run at Silver Springs State Park on February 28, 2026, featuring a children's area, refreshments, age-group medals, team awards, and proceeds that fund local septic maintenance grants.

The Gator Dash Trail Run will take place in Southwest Jacksonville on Sunday 1 March 2026. You can run between 10 and 21 kilometers.

Run the 1st Annual Archie's Pizza Mile Trail Style in Williston FL on March 7 for a lively three loop beer mile with a non alcoholic option and finisher medals. Trail running, pizza vibes, and awards for overall winners.

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.

A youth trail run at Princess Place Preserve on March 21, 2026, with races for ages 3 to 13 over three distances. The flat, mostly hard-packed course offers timing, wooden finisher medals, water stations, and age-group awards.

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.