Kentucky
Kentucky Trail Running Calendar 2026-2027
Explore the best trail runs in Kentucky for 2026-2027! Our updated list features 66 exciting trail runs across the region. Find your next trail run in Kentucky below and join the trail community at these great events!
October 2026
Trail races of 5K, 10K and half marathon at French Shelter Park on October 31, featuring themed costumes, finisher medals and series points.
Local road races in Bowling Green, KY on October 31, 2026 offering 5K, 10K and a half marathon with finisher medals and posted results. EMS is not on site and water stations are limited.
November 2026
A community Turkey Trot in Wendell Moore Park offering a 5 mile run and a 4K walk with chip timing, finish medals, and awards including overall male and female prizes.
Trail races at General Butler State Resort Park on 11/07/2026 include 5K, 10K, 13.1 mile, 20K relay and a 6 Hours of Power loop event with park facilities and river overlook.
Junior Achievement Chilly Hilly Trail Run in Henderson, KY on November 7, 2026 offers 5K and a new 10K on park trails, with event t-shirts and early-bird perks.
A 5K and Half Marathon at Active Heroes Retreat in Shepherdsville, KY on wooded trails and gravel roads supporting military members and veterans.
Gobbler races in Bowling Green, KY on November 14, 2026 offer 5K, 10K and a half marathon with listed registration fees. The event provides finisher medals and results, with limited on-site EMS and water at lap ends and the finish.
Turkey Trails in Hamilton, OH offers on-site and virtual races from a kids dash to a half marathon, with shirts, bibs, medals, timing, and finish-line food.
A 4 mile trail race at Veterans Park in Lexington on November 14, 2026, chip timed with awards and proceeds benefiting the Hickman Creek Conservancy.
Trail races in Red River Gorge on November 14, 2026, offering a 30K and a 50 mile option with poles recommended.
A 5K Run and Ruck on November 14, 2026 in Wilmore, Kentucky where 100% of proceeds support Thomson-Hood Veterans Center.
A 24- and 12-hour endurance event at Belfry High School featuring a 1-mile loop, relay and rucksack divisions, chip timing, on-course support, and awards by category.
A 2 mile fun run at Huntertown Community Interpretive Park in Versailles, KY on November 21, 2026, run as two laps on a mowed grass cross-country style trail with minimal elevation.
Trail half marathon at Jefferson Memorial Forest in Louisville with steep climbs, aid stations at miles 2 5 8 and 11, and an out-and-back route on the Siltstone Trail.
Trail races at Harrods Creek Park in Prospect KY offering 5K one lap and 10K two laps with proceeds supporting park upkeep.
A Thanksgiving trail event at Pulaski Park in Nancy, Kentucky on November 26, 2026 featuring a 5K and a 1 mile fun run with proceeds benefiting the American Cancer Society and awards for overall, age group, and team divisions.
A Thanksgiving weekend road event in Bowling Green, KY offering 5K, 10K, and a half marathon with finisher medals and posted results, run as a locally organized race with limited on-site services.
A last person standing backyard ultra in Bloomfield KY with repeated 4.167 mile loops through town; registration is full and a waitlist is available.
December 2026
A two-day trail event at Camp Crooked Creek in Shepherdsville KY with a 12.7 mile loop and race options from 5K up to 100 miles.