Kentucky
Kentucky Trail Running Calendar 2026-2027
Explore the best trail runs in Kentucky for 2026-2027! Our updated list features 53 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
Experience a scenic trail run through the Red River Gorge on a private looping course. This cup less half marathon supports local search and rescue teams while offering a festive atmosphere with medals and post race meals.
An annual military fitness tribute at Queenslake Horse Farm in Georgetown, Kentucky honoring the 19 fallen heroes with a weight carrying challenge and a full day music festival.
Trail runs at Jefferson Memorial Forest with an 8-mile route and a 5-mile option, cupless hydration, on-course water for the 8 miler, restroom facilities, awards for overall male and female, and a virtual option.
An exclusive nighttime 2.6 mile run in downtown Cincinnati offering early access to select BLINK installations and an interactive art experience.
Experience a unique trail run through the hills and woodlands of Gravel Switch. Enjoy a route featuring meadows and steep climbs followed by a pancake breakfast and handmade awards at the local heritage festival.
Experience a scenic trail run through the hills of Kentucky at the historic Bill Monroe Homeplace. This event features 5K, 10K, and 25K distances accompanied by live bluegrass music and on site camping.
A weekend of races at the Gallatin County Fairgrounds in Glencoe, Kentucky featuring an 800 m kids run, a 5K trail with a two hour cut off, and a last runner standing ultra run on repeated 2.083 mile laps. Headlamps required for the ultra.
A second-annual fall 5K hosted by Gleaning Housing at Coldstream Park / Legacy Trail in Lexington, KY, with pumpkins for donors and snacks and drinks for all participants. Participants may bring or wear a pumpkin costume.
Experience a 22 km trail run crossing both the Lake Barkley and Kentucky Lake bridges. Participants can run the full course individually or join a two or three person relay team through the Land Between the Lakes Recreation area.
Two trail races, 50K and 25K, take place at Mammoth Cave National Park on October 24, 2026 starting from Bell's Tavern Pavilion. The crushed gravel out and back course has ascents and descents, cupless aid stations, and limited entries.
Timed 5K and 10K trail run and walk at Red Wolf Sanctuary in Rising Sun, Indiana, with courses through waterways, wetlands and past wildlife enclosures and proceeds supporting the sanctuary's conservation work.
Experience Cincinnati longest running ultramarathon at the Stone Steps 50K and 27K Trail Run. Take on the wooded paths of Mt. Airy Forest in this historic event held just miles from downtown.
Little Batty Trail Runs on 10/25/2026 in Nancy, KY features trail courses of 13.1 miles, 10K and 5K with creek or dry lake bed crossings, cross country sections and a short pavement segment; registration runs 3/20 to 8/31/2026.
Experience a themed trail run through Cincinnati's French Shelter Park with options for a 5k or 10k distance. Participants enjoy costume contests and holiday activities while earning points toward a global series award.
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.
Turkey Trails Cincinnati presents in-person and virtual running options on 11/14/2026 in Hamilton OH, from a 50 m kids dash up to a half marathon. Event features include chip timing, shirts, custom bibs, medals, free photos, and finish-line treats.
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 offering a 30 km option and a 50-mile course with notable climbing; registration opens June 1, 2026.
24 hour and 12 hour endurance event at Belfry High School on a one mile loop with chip timing, rucksack division, team and individual categories.