Kissimmee
Trail Running Calendar near Kissimmee 2026-2027
Explore the top trail runs near Kissimmee for 2026-2027! We've gathered 16 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Obstacle course weekend at Lake Nona in Orlando featuring a 5 km Sprint, 10 km Super, kids races, workshops and a 4 hour Hurricane Heat.
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.
November 2026
Thanksgiving themed 5K and kids dashes at Southern Hills Farm in Clermont with chip timing, finisher medals, free local coffee and apple cider donuts.
Turkey Day 5K Clermont is a Thanksgiving themed 5K at Waterfront Park in Clermont, FL, featuring finisher medals, race swag, and an out-and-back course on the Upper Tampa Bay Trail.
December 2026
Test your endurance with 6 hour, 12 hour, or single loop races on a 4.17 mile grass and asphalt course featuring a full Runners Village and grilled food.
January 2027
Six hour trail challenge in Clermont where runners complete a 5K each hour; four and five laps earn patches, six laps earn a medal and national leaderboard ranking.
Multiple distance trail event in Christmas, Florida on January 30 and 31, 2027, featuring rarely traveled single track through several state forests and notable birdlife.
February 2027
Valentine's Day 5K at Southern Hills Farm in Clermont with chip timed 5K, chocolate treats at the finish, and kids dash options for families.
March 2027
A chip timed 5K at Formosa Winery in Kissimmee FL on March 14 2027 with wine tasting, cider, a finisher medal and results by J3 Timing.
April 2027
A backyard ultra at Lake Louisa State Park where runners complete a 4.167 mile loop each hour until they stop, capped at 200 entrants with a waitlist.
May 2027
June 2027
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.