Trail Running calendar near Chiefland 2025-2026

Croom Zoom is a scenic trail run in Brooksville's Croom Park through oak hammocks and tree canopy, with 50K, 20 mile and 10 mile options. Entries cap at 250, so register by January 1, 2026 to secure your spot and chase a finisher award.

Run scenic single track through Jennings State Forest near Middleburg Florida with options from 7K to a challenging 50K. Enjoy creek crossings, vistas above Black Creek and technical climbs on the Pioneer Trail for a true trail experience.

Join the Masaryk Wine Run 5K at Masaryk Winery for a scenic vineyard run with chip timed results and free race photos. Participants get a tee, shatterproof collapsible wine glass, a finisher medal that doubles as a bottle stopper and a pour..

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.

Join the Florida Run at Manatee Springs State Park for scenic trail races through cypress and clear spring water, with half marathon, 10K and 5K options. Enjoy beautiful views and the chance to spot manatees in the wild.

Run through Ocala in the Painted Horse Urban Ultra, an untimed urban adventure and scavenger hunt with 55k and 25k loop courses visiting dozens of painted horse installations. Navigation heavy and mostly self supported.

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.

Florida Death Race on March 7, 2026 is a brutal point to point trail challenge along the Florida Trail and Suwannee River. Pick 74 or 37 mile courses and carry a signature 1 lb railroad spike to toss at the finish.

Run single loop trails along the Withlacoochee River and through serene forest at the Long Play Trail Run in Brooksville. Choose from a 33.3 mile race, a half marathon or a 6K and earn a collectible vinyl record finisher award.

Escape to the Juniper and Hopkins Prairies for a scenic out and back ultra in Ocala National Forest, with 50K and 30K options. Entry is free, the field is capped at 50, registration opens Dec 1, 2025, and carpooling is encouraged.

Run a 5k or 10k on the flat, fast Archer Braid Trail in Archer, Florida on Saturday March 28, 2026. Enjoy a peaceful paved out and back course with professional timing and age group awards, plus free entry for Florida Track Club members.

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.

Run the 30th Croom Fools Run on April 4 2026 in Withlacoochee State Forest near Brooksville Florida. Choose 16 mile 50K or 50 mile looped trail routes through pines creeks and cypress ponds with a capped field of 250 runners.

Run for a cause at the Safe Animal Shelter Fundraiser Trail Run in Middleburg FL on April 12, 2026, featuring scenic flat trails on Sandridge Trail and 5K, 10K and half marathon distances. Proceeds support Safe Animal Shelter and every entr..

Run the Withlacoochee Trail Marathon on April 19 in Hernando on scenic forest trails with marathon, half and 10K options. All finishers earn an award and every entrant gets a cotton shirt and bib.

Run the Skunk Ape in Ocala FL on April 25 to 26 with 50 Mile or 100 Mile options on scenic trails. Expect sandy single track through pine woods and lakes, strong aid station support, with a buckle for 100 Mile runners.

Hit the trails on May 24 in Inverness FL for Sweat, Swat n Swear offering single loop 50K, 25K or 10 Miler courses through the scenic Citrus Tract at Holder Mine Campground. Expect aid stations, a finisher award and a lively post race picni..

Run under the stars in the Withlacoochee Forest at the Hot August Night Trail Race on single track packed with sand and pine needles. Headlamps required; all finishers get a handcrafted medal and a post race picnic.

Run scenic single track trails and rolling hills at San Felasco Preserve in this benefit trail race benefiting Friends of San Felasco. Choose 25k or 50k with aid stations, a TailGate2Gate celebration and custom finisher medal and glass.

Experience oak lined trails along the Suwannee River at the Wild Florida Trail Run in White Springs with 50K, 25K and 10K routes finishing at Stephen Foster Folk Culture Center State Park. Race supports the Florida Trail Association.