Kissimmee
Trail Running Calendar near Kissimmee 2026-2027
Explore the top trail runs near Kissimmee for 2026-2027! We've gathered 13 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Orlando Spartan Weekend at Lake Nona brings multiple obstacle races and activities over a weekend, including 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
A Thanksgiving day event in Clermont with a chip-timed 5K that includes a shirt, medal, and apple cider donut plus kids races and a family-friendly post-race gathering.
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
Loop event at Lake Wailes Park offering 4.17 mile, 6 hour, 12 hour, and 12 hour relay options with aid stations and awards.
January 2027
A multi-distance trail event in Christmas, Florida on January 30 and 31, 2027, running through Tosohatchee and nearby state forests with single track, varied terrain, wildlife viewing, course maps, aid station details, and crew and volunteer support.
February 2027
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 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.
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.