Kentucky
Kentucky Trail Running Calendar 2026-2027
Explore the best trail runs in Kentucky for 2026-2027! Our updated list features 59 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
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.
Four mile trail race at Veterans Park in Lexington on Nov 14, 2026 with chip timing, age group awards, commemorative shirts, and a virtual participation option.
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 with a one mile loop, chip timing, relay and rucksack divisions, onsite food, porta potties and camping.
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.
A trail half marathon at Jefferson Memorial Forest in Louisville featuring steep climbs and aid stations at miles 2 5 8 and 11; refunds are not available.
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, Kentucky where runners repeat a 4.167 mile town loop each hour until one runner remains.
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.
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.
Trail races at Otter Creek Park, Brandenburg KY, on December 19, 2026, featuring marathon, 16-mile and 8-mile loop courses with aid stations and a chili cook-off.
Local road races in Bowling Green, KY on December 26, 2026 offering 5K, 10K and a Half Marathon with timed results and finisher medals; limited on site medical coverage and water stations.
January 2027
A winter event in Bowling Green on January 2, 2027 offering a 4 mile run (two laps on a gravel perimeter track) and a 2 mile walk with walking only rules. Entry fee is $40 and each paid participant receives a sweatshirt or hoodie.
Trail races at Pulaski County Park on January 9, 2027 offering 5K, 10K and half marathon courses with rolling hills, finisher medals and no on course aid.
New Year road races in Bowling Green on January 9, 2027 offering 5K, 10K and a 13.1 mile half marathon with finisher medals and limited on course support.