Trail Running Calendar Kentucky 2026-2027

Join the Raven 10K on Sunday, September 27, 2026 for a scenic trail run through Raven Run Nature Sanctuary near Lexington, KY. Choose in person or virtual entry and tackle a challenging 10K in a beautiful park setting with limited field.

Experience the Rugged Red Trail Half Marathon in Red River Gorge on October 3, 2026. Tackle 13.1 miles on site or virtually, earn a long sleeve shirt and finisher medal, enjoy BBQ and beer, and support local search and rescue.

Join the first Running Pumpkin 5K in Lexington on October 17 at Coldstream Park and Legacy Trail, a fun autumn run hosted by Gleanings Housing to support affordable housing. Bring or wear a pumpkin and enjoy snacks and community spirit.

Run a scenic 22 km course from the Lake Barkley Bridge to the Kentucky Lake Bridge through the Land Between the Lakes in Hardin, KY. Solo runners and 2 or 3 person relays welcome for a memorable bridge to bridge challenge.

Join the Legends Spooky Trail Race in Owensboro on October 25, 2026 for a scenic, spirited 6 km through Rudy Mines on the Ben Hawes Trail. Two 3 km loops over rolling hills, rooty singletrack and a final climb make this an autumn trail chal..

Hit the haunted trails at French Shelter Park on October 31 for a festive 5K or 10K with costume fun, family games and gift card giveaways. All finishers receive a custom T shirt and medal and live prizes include a best costume award.

Join Medal Madness on December 12, 2026 at Ephram White Park in Bowling Green for a festive 5K, 10K or half marathon on scenic gravel out and back loops. Expect finisher medals, a gear shop, awards and a best costume contest.