Kissimmee
Trail Running Calendar near Kissimmee 2026-2027
Explore the top trail runs near Kissimmee for 2026-2027! We've gathered 17 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
An evening Halloween 5K in Clermont on October 31, 2026, with spook zones, a costume contest, a DJ, a kids' trick-or-treat trail, and a virtual 5K option.
November 2026
A family-focused Thanksgiving 5K at Southern Hills Farm with chip timing, kids dashes, on-course entertainment, and local food offerings.
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
Timed 12 hour, 6 hour and 4.17 mile events plus a 12 hour relay on 4.17 mile loops around Lake Wailes in Lake Wales, FL.
January 2027
A six-hour trail challenge in Clermont, FL where runners complete a 5K each hour for up to six rounds, earning patches, a medal, and leaderboard placement.
Forgotten Florida is a trail running event in Christmas, FL on January 30 and 31, 2027 with 100, 50, 15 and 8 mile courses through seldom used state forest trails.
February 2027
A Valentine’s Day 5K at Southern Hills Farm in Clermont with chip timing, finish line chocolate treats, and kids dashes.
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 event at Cady Way Trail Head offering 5K, 10K, half marathon, marathon and 50K lap races with hand timing and a 9.5 hour time limit.
October 2027
Obstacle course weekend at Lake Nona on Oct 9 and 10, 2027 featuring Sprint 5K, Super 10K, kids races and spectator options.