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.
November 2026
Thanksgiving 5K and kids races at Southern Hills Farm featuring chip timing, finisher medals, an apple cider donut, free coffee and ice cream.
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
Multi-format running event at Lake Wailes Park on Dec 19, 2026 offering 12h, 6h, 4.17 mile, and 12h relay races on 4.17 mile loops with aid stations.
January 2027
A timed 6 hour trail challenge at Lake Louisa where runners complete a 5K each hour, earn patches or a 6 inch medal, and compete on a world leaderboard.
Trail running event in Christmas, Florida on February 6 and 7, 2027 with distances from 8 to 100 miles on rarely used single track through several state forests.
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 stair-climbing fundraiser at City National Bank Tower in Orlando on March 6, 2027 with 512 steps supporting the American Lung Association.
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
Two days of Spartan obstacle racing at Lake Nona, Orlando featuring sprint, super, kids races, a Hurricane Heat option and spectator access.
Halloween themed 5K in Clermont on 10/30/2027 with in person and virtual options, spook zones, a costume contest, live DJ, and a kids trick-or-treat trail.