Trail Running calendar near Osteen 2026-2027

Timed trail event in Palm Coast with 6 hour and 12 hour options on a flat, shaded one mile loop and a stocked aid station.

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 free, non-competitive 50-mile group run through St. Augustine on Aug 22, 2026, with flexible distances, coaching support, post-run refreshments, and event giveaways.

A trail half-marathon event in the Green Swamp West Tract offering a run and a ruck division, aid station at the turnaround, finisher glassware, and a post-race potluck.

Back to School Bash is a themed trail run at Central Florida Bible Camp offering one- or two-loop options and ten field day activity stations.

A timed lake-lap endurance event in Lakeland FL with 12-hour, 6-hour and 12-hour relay formats and 2.84 mile laps.

A 3 miles obstacle course at Camp Winona in De Leon Springs with over 17 obstacles, race T-shirt, finisher's medal and a pancake breakfast; two pricing periods apply.

A race day at Jay Blanchard Park on 09/27/2026 with distances from a 50 m kid's dash to a 13.1 mile half marathon, chip timing for main races, event shirts and medals, plus volunteer and virtual options.

A 5K at Wickham Park in Melbourne with in-person and virtual options, finisher medals, age-group and team awards, and proceeds benefiting Florida Wildlife Hospital.

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.

Orlando Spartan Weekend at Lake Nona features sprint and super obstacle races, kids events, a Hurricane Heat and an obstacle workshop across Oct 9 to 11, 2026.

Lutheran Counseling Services holds the We Care 5K on October 10, 2026 in Longwood to raise funds and awareness for mental health. The event offers an in person 5K along parts of the Seminole Trail and a virtual 5K option.

The Itch is a point to point 50K on the Florida National Scenic Trail West Corridor on October 17, 2026, running from Lake Kerr Road CR-316 to the Baseline Road Trailhead in Ocala. The route uses trail blazes, has on course aid and one drop..

A 5K event at DeLeon Springs State Park offering in-person and virtual options, chip timing, race shirt and medal, and fundraising support for Friends of DeLeon Springs State Park.

A dog friendly off-road 5K at Rock Springs Run State Reserve in Sorrento, FL on October 24, 2026. Registration includes park admission, a t-shirt and finisher medals for runner and dog, with limited in-person spots.

Trail races in Palm Coast, FL on October 25, 2026 offering 12K, 24K and 50K on mostly single track near the Atlantic, limited to 125 runners.

Experience the famous clay trails of Clermont in this hilly off road event featuring timed 15K and 5K distances. Run along scenic 5 Mile Road and enjoy a professional racing environment with full course support and finisher medals.

A Halloween 5K in Clermont with haunted spook zones, a costume contest, and a live DJ. A virtual 5K option includes shirt, bib, medal and domestic shipping.

Oct 31, 2026 in Lake Wales FL a backyard ultra where runners complete a 4.167 mile loop every hour until one runner remains.

A chip-timed trail run at Lake Louisa State Park on November 7, 2026 offering 5K, 10K and half-marathon distances with aid stations and on-course restrooms.