Trail Running calendar near Chiefland 2026-2027

Moon Over Croom is a running event on June 6, 2026 presented by Trailhead Ultras with three distance options: 21M, 14M, and 7M. The event is organized by Tampa Races.

Experience the Withlacoochee Forest after dark in this night trail race featuring 5, 10, and 20 mile distances. Navigate single track trails under the stars with glow stick markers and a post race picnic celebration.

A five hour Fat A$$ event on Section 4 of the Pioneer Trail in Middleburg Florida where participants run an out and back loop of about 2.5 miles as many times as possible. Limited field and cupless format with minimal aid provided.

An 8 hour timed trail event at Ross Prairie featuring a 6.5 mile berm loop through sandy fire lines, pine forest and prairie. The event offers on site camping, self crewing space and is organized by a veteran owned race company.

S.O.S. in Middleburg, FL uses a 2.75 mile Sandridge Trail loop with a 9K plus 3, 6 and 12 hour timeframes and ruck options. It is a cupless event with aid stations, hot food, awards, and proceeds benefiting local recovery nonprofits.

The John Holmes Trail Run takes place at Croom Park and Withlacoochee State Forest on October 3, 2026, offering 50K, 16 mile and 9 mile options. The field is limited to 250 runners and this is the event's 34th running.

A point-to-point 50K on the Florida National Scenic Trail Western Connector near Ocala with required GPX navigation, on-course aid stations, and one drop bag location; runners must carry a phone and follow orange blazes.

Trail race at San Felasco Hammock Preserve near Alachua offering 25K and 50K loops on single track and double track trails with fields and hills. Net proceeds support Friends of San Felasco and finishers receive a custom medal and glass.

An evening trail event on October 24, 2026 in Ocala offering 5K and 10K run and ruck options plus a combined challenge, with ruck weight standards, finisher medals, and sections on the Florida Trail.

Trail running event in White Springs, Florida offering 50K, 25k and 10k distances with aid stations and cutoffs. Races finish at Stephen Foster Folk Culture Center State Park and benefit the Florida Trail Association.

A trail ultramarathon at Dunns Creek State Park featuring an approximately 11.75 mile loop through pine and scrub, multiple distances up to 100 miles, two aid stations and a runner's village with parking and camping.

A looped ultramarathon at Ravine Gardens State Park in Palatka offering 12-hour, 24-hour, 50K and 50-mile options on a USATF measured 2 mile paved course through a wooded ravine. Night running requires personal lighting.

A backyard ultra at San Felasco Hammock Preserve State Park where runners repeat a 4.167-mile loop every hour until one completes a loop no other does. No on-course aid, limited base camp space, and basic facilities at the start/finish.

A set of runs on November 21, 2026 in Brooksville, Florida features a 5K trail run, a 2.5K Turkey Trot with costumes encouraged, and a short Color Fun Run with colored powder. Proceeds support Scouting programs.

A multi-distance trail event in Middleburg FL on a scenic 7.2 mile loop offering 100 mile 50 mile 35 mile 14 mile and 7 mile options. The cupless race features staffed aid stations and a custom buckle for 100 mile finishers.

A chip timed 5 km run and walk at Masaryk Winery in Masaryktown, Florida on January 16, 2027, with a helper registration option, race items including a t-shirt and wine glass, and results posted online by J3 Timing.

Trail races on the Pioneer Trail in Jennings State Forest near Middleburg FL, featuring 50K, marathon, 12K and a 7K closer to five miles. Courses use diverse single track with technical sections, aid stations about every 2.5 to 3 miles, and..

A relaxed 12 hour trail event at Whispering Pines City Park in Inverness, FL, featuring a marked 5 mile loop, an aid station potluck, and finisher awards for at least 10 miles. Capacity is 185 runners.

Sombrero Ultra Running Festival in Middleburg, Florida is a multi day ultrarunning weekend with timed events from three hours up to 48 hours plus 48 hour team relays. The festival includes a runner village, a single aid station, on site med..

Trail races at Manatee Springs State Park on February 19 and 20, 2027 include 5K, 10K and a half marathon on smooth, shaded trails. Weekend bundle options include a special finisher item and race swag.