Kentucky
Kentucky Trail Running Calendar 2026-2027
Explore the best trail runs in Kentucky for 2026-2027! Our updated list features 75 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 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.
Trail run at John James Audubon State Park on November 7, 2026 offering a classic 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.
A Thanksgiving themed trail event in Hamilton, Ohio offering races from a 50 m Kids Dash to a half marathon, plus a virtual option and race swag.
A 4 miles trail run and walk at Veterans Park in Lexington on November 14, 2026, over mostly hard-packed dirt trails with grassy and short paved sections. The race is chip timed, offers awards, hydration stops, and a virtual option with mailed shir..
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 hour and 12 hour endurance event at Belfry High School offering individual, relay and rucksack divisions on a 1 mile loop with chip timing and on-site facilities.
A two mile fun run in Huntertown Community Interpretive Park run as two laps on a mowed grass trail, with food trucks after the event and a T‑shirt deadline of Nov 1.
A trail half marathon at Jefferson Memorial Forest near Louisville, KY, featuring steep climbs, multiple aid stations, and organized by Headfirst Performance.
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.
Backyard Ultra in Bloomfield, Kentucky where runners repeat a 4.167 mile loop each hour until one runner remains.
December 2026
Experience an exclusive trail event at the Harry S. Frazier Scout Reservation featuring looping courses through Kentucky forest and a runner's village by John Barr Lake with distances from 5K up to 100 miles.
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 in Louisville offering a 6.6-mile loop and a half marathon plus virtual options. The event is cupless, has an aid station about halfway, on-site restrooms, limited parking, and overall male and female awards.