Kentucky
Kentucky Trail Running Calendar 2026-2027
Explore the best trail runs in Kentucky for 2026-2027! Our updated list features 77 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
STADIUMTREK at Nippert Stadium on October 2, 2026 features an individual challenge to complete 14,000 steps within a three hour window for 14ER status, plus a relay for teams of 2 to 4. Registration opens June 17, 2026 and the fee is $49.99.
Trail Half Marathon in Slade, Kentucky featuring a 13.1 mile loop in the Red River Gorge with commemorative shirt, medal, awards and on-site amenities.
A 1.8-mile military-style obstacle challenge at Queenslake Horse Farm on Oct 3, 2026 honoring the 19 fallen with memorial stations and a lakeside 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.
A 2.6-mile untimed nighttime run in downtown Cincinnati with early access to select BLINK installations, beginning and ending at Elm Street Plaza.
A local road race in Bowling Green on October 10, 2026 offering 5K, 10K, and 13.1 miles options; registration fees vary by distance and race day services are limited.
A hilly trail 5K in the Forkland Community with a pancake breakfast and T shirt included, handmade awards, and new 70+ age group recognition.
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.
Multi-race weekend in Glencoe KY featuring an 800 m kids run, a 5K trail and a last runner standing mini ultra, held October 16 to October 20, 2026.
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.
A 13.6 mile point to point trail run across Lake Barkley and Kentucky Lake bridges, with two and three person relay options and leash required dogs welcome.
Community 5K on October 17, 2026 at Thomas Nelson High School supporting the Imagination Library and Nelson County Schools UP Foundation; free entry and optional donations.
Four 5k events at Perry County Park on Oct 23, 2026, with family friendly paved routes and a haunted trail, supporting the Hazard Police Department Shop with a Cop program.
Local road races in Bowling Green on 10/24/2026 offering 5K, 10K, and a 13.1 mile half marathon with finisher medals and posted results. Registration fees vary by distance.
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.
Trail 5K and 10K at Red Wolf Sanctuary in Rising Sun on October 24, 2026; timed event with shuttle parking and proceeds supporting the sanctuary.
A 5K trail race at Silver Creek Bike Park in Berea KY on October 24 2026 with on course photography, water fill station, post race snacks and a cupless low waste policy.
A no-contact Zombie 5K paired with an Autumn Fun Fest featuring a vendor fair, costume contest, games, and a pet supply drive to benefit local animal care.
Trail races in Mt. Airy Forest near Cincinnati offering 50K and 27K loop courses with marked trails, aid stations, chip timing, and race shirts.
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.