Trail Running calendar near Ocala 2026-2027

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.

Point to point trail races in Volusia County offering 50 mile, 50K and 17K courses that finish at Central 28 Beer Company in DeBary, Florida.

A trail event in Middleburg, Florida on the Pioneer Trail offering a 50K, marathon, 12K and 7K. Courses feature varied single track, technical sections, stream crossings and mapped GPX files, with aid stations and time limits for each dista..

A donation based 12 hour trail event in Inverness, FL on a 5 mile loop with packed sand and pine needle surfaces. The course is marked and supported by an aid station with a communal potluck; capacity is 185 runners.

A fundraising 5K in Ormond Beach with in-person and virtual options. Proceeds benefit The Heterotaxy Connection and registration includes chip timing, a shirt, and a finisher medal.

A multi-format timed running festival in Middleburg, FL offering 3/6/12/24/48-hour events and relays, a cupless single aid station with hot food, on-site medical and footcare support, runner village and RV parking with no hookups.

Trail races and a virtual option follow the Lake Apopka North Shore Loop Trail from Magnolia Park, with distances from 5K to 30K, cupless format and required personal hydration.

Trail-run, hike and walk options from 5K to half marathon through Seminole State Forest near Sorrento, FL. The event is a charity sponsored by Tracked Chair Adventures, Inc., a nonprofit 501(c)(3), with published registration fees and dates..

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.

An obstacle course racing weekend at Diamond D Ranch in Jacksonville featuring Sprint and Super races, kids races, trail distances, team starts, and spectator access.

A community 5K at Marion County Airport in Dunnellon that combines varied trail surfaces and the sights and sounds of aircraft. Age-group medals and a Traveling Cup for the fastest team are part of the event.

Trail races at Diamond D Ranch near Jacksonville mix mostly non-technical terrain with occasional muddy, ankle-biting sections and options for 10K and half marathon distances.

Experience a unique single loop trail run through the Withlacoochee State Forest featuring 33 1/3 mile, half marathon, and 6K distances. Enjoy riverside trails and celebrate your finish with a post race barbecue and handcrafted medals.

A chip timed 5K run/walk at Formosa Winery in Kissimmee on March 14, 2027. Registration includes a T-shirt, a medal that doubles as a bottle opener, a pour of cider and a homemade cider donut.

First held in 1967, this Easter-themed beach run at the Daytona Beach Bandshell features professionally chip timed 4 mile and 2 mile events plus kids dashes and participant medals.

Trail races at Silver Springs State Park include a half marathon, 10K and 5K plus a virtual half marathon option. Participants receive a tech shirt and finisher medal, the bib serves as park entry and awards cover overall and age groups.

A team-based adventure in New Smyrna Beach where two-person teams tackle 20-plus obstacles including puzzles and physical tasks. Participants must wear the event shirt and bib; racers must be at least 10 years old.

Turtle Trot is a 5K run and walk at SunWest Park in Hudson, Florida, with a paved course around old salt mines. Proceeds support Pasco County's PAIR program and every registered participant receives a finisher award.

A backyard ultra at Lake Louisa State Park on April 10, 2027 where runners complete a 4.167 mile loop each hour until they can no longer start a loop; shirts, medals, ribbon sliders, and multiple award categories are offered.

Trail marathon, half marathon, and 10K on unpaved Withlacoochee State Forest trails with three aid stations and mandatory personal hydration; primitive camping is available near the course.