Kentucky
Kentucky Trail Running Calendar 2026-2027
Explore the best trail runs in Kentucky for 2026-2027! Our updated list features 64 exciting trail runs across the region. Find your next trail run in Kentucky below and join the trail community at these great events!
November 2026
A 5 mile trail and paved course at Wendell Moore Park with a 3 mile walker option, age group awards, t shirts for early registrants, and door 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.
November 7 trail run at John James Audubon State Park offering a 5K and a new 10K, with proceeds benefiting Junior Achievement of West Kentucky.
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.
Thanksgiving-themed races in Hamilton, OH on 11/14/2026 offering Kids Dash, 1 mile, 5K, 10K, half marathon, virtual and volunteer-then-run options.
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 event at Camp Crooked Creek in Shepherdsville KY offering a 5K trail around John Barr Lake with a $15 registration fee and packet pickup.
Holiday 5K 10K and half marathon in Bowling Green KY on 12/12/2026 with finisher medals, official results, and limited on course support.
Trail races at Waverly Park offering a roughly 6 to 6.5 mile loop and a half marathon, with on-site packet pick-up, an aid station, and a virtual option.