Trail Running calendar near Osteen 2026-2027

Nighttime trail running at Colt Creek State Park with looped unpaved courses offering a 5K, a 10K, and a combined 15K challenge. 5K starters must use a headlamp and virtual entries receive mailed race items.

Trail races at Lake Apopka from 5K to 30K on packed lime rock and hard-packed Northshore trails, with support stations and awards; starts and finishes at Magnolia Park.

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..

Multi-distance ultramarathon along Florida's Space Coast and Treasure Coast, limited to 100 runners and requiring support crew.

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 event at Holloway Park near Lakeland, FL offering 10k, 30k, 50k and a five person relay on a groomed cross country course.

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.

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 runs at Colt Creek State Park traverse pine forests, lakeshores and meadows with 5K, 10K and Half-Marathon options. The event includes aid stations, on-course restrooms, chip timing, event swag and team awards.

A point to point 5K in Winter Park with a final mile on a tree canopied dirt road, event swag, reusable-cup hydration options, and a tree sapling for in-person finishers.

Stomp Out Suicide is a shaded trail run and walk at Withlacoochee River Park on May 15, 2027, offering 10K, 5K and 1 mile distances and focusing on raising awareness about suicide; participants receive shirts, snacks, and finisher awards.

Trail races in Inverness, FL with single-loop courses through Withlacoochee State Forest offering 50K, 25K and 10-mile distances and staffed aid stations.

Two-day running event on June 26 and June 27, 2027 at Cady Way Trail Head in Winter Park, FL. Distances range from 5K to 50K on flat, looped paved trails with a pavilion aid station and hand timing.