Trail Running calendar near Kissimmee 2026-2027

A mid June trail run at Lake Louisa State Park offering 4 mile and 8 mile loop options with chip timing, live music, throwback swag, aid stations, and on-course restrooms.

Independence Double is a two-day running event in Winter Park, FL on June 27 and 28, 2026, offering 5K, 10K, half marathon, marathon, and 50K distances with single-day and both-days registration options.

A multi-distance ultramarathon based at the Environmental Learning Center in Vero Beach, Florida, built around eight out and back arms. Distances range from a 5K to 100 mile and finishing all arms within 32 hours earns an Octopus Buckle.

A 30K night trail race in Green Swamp West Tract near Dade City, Florida on July 18, 2026, with varied Florida terrain, aid stations every 3 to 5 miles, a post-race potluck and finisher glass options.

A multi-distance event at Blue Jacket Memorial Park offering in-person and virtual options, chip-timed 5K/10K/half distances, youth pricing, participant shirts and medals, free photos, and finish-line ice cream.

Summer Sizzler in Tampa on 08/01/2026 features timed 5K 10K and 15K races, untimed 1 mile and kids dash, and a virtual option. The event includes chip timing, shirts and medals, free photos and finish line treats.

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 night trail half-marathon at Green Swamp West Tract on September 12, 2026, with an aid station at the turnaround, no formal cut-off, awards for top finishers, participant finisher items, and a $25 post-race potluck.

Trail run at Central Florida Bible Camp in Eustis with a roughly 3.2 mile two loop option and a single loop fun option. Runners can attempt up to ten field day stations such as inflatable obstacles, axe throwing, and cornhole.

Tick Tock Ultra is a timed running event on September 19, 2026 offering 6 hour and 12 hour formats plus a 12 hour five person relay, organized by Ultra Ultras with registration via UltraSignup.

A timed lake-lap event at Lake Hollingsworth offering 12 hour, 6 hour and 12 hour team relay formats on 2.84 mile paved laps. The race has a hard cap of 200 entrants and supports the Pheel Good Foundation.

A multi distance running event in Tampa with a half marathon, 10K, 5K, 1 mile, kids dash and virtual option. Features include chip timing, designer shirts and finisher medals, with youth pricing for ages 12 and under.

The Camp Winona Mud Fest will take place in De Leon Springs on Saturday 26 September 2026. You can run 3 miles.

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.

An in-person 5K and virtual 5K held at Wickham Park, with packet pickup the day before, finisher medals or reduced fees for no medal or no shirt, post-race refreshments, giveaways, and awards across age groups and teams.

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 on October 10 and 11 offers obstacle races from a 5 km Sprint to a 10 km Super, plus kids races, a workshop, and a four hour Hurricane Heat. Team registration and a GOVX service discount are available.

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.

A point-to-point 50K trail race on the Florida National Scenic Trail West Corridor, The Itch requires runners to navigate by orange blazes, carry a GPX file and a phone, and plan their own transport between start and finish.

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.