Kentucky
Kentucky Trail Running Calendar 2026-2027
Explore the best trail runs in Kentucky for 2026-2027! Our updated list features 76 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
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 trail half marathon with two and three person relay options that crosses Lake Barkley and Kentucky Lake via the Central Hardwoods Scenic Trail.
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.
A Halloween themed event at Saunders Springs Nature Preserve offering an in person 5K, a virtual 5K, and a free kids mile with medals and costume prizes.
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 themed 5K run/walk at Lone Oak Green Park in Nicholasville on 10/24/2026 with supply stickers at each 1K and staged no-contact zombies along the course.
Trail running in Mt Airy Forest, Cincinnati with looped single track courses: a 50K over seven loops and a 27K over four loops, about 5,200 feet of climbing.
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.
Two-loop trail race at Rudy Mines near Owensboro covering about 6 km on dirt and packed trails with hills, switchbacks and some rocky sections.
Trail races of 5K, 10K and half marathon at French Shelter Park on October 31, featuring themed costumes, finisher medals and series points.
Local road races in Bowling Green, KY on October 31, 2026 offering 5K, 10K and a half marathon with finisher medals and posted results. EMS is not on site and water stations are limited.
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.
Junior Achievement Chilly Hilly Trail Run in Henderson, KY on November 7, 2026 offers 5K and a new 10K on park trails, with event t-shirts and early-bird perks.
A 5K and Half Marathon at Active Heroes Retreat in Shepherdsville, KY on wooded trails and gravel roads supporting military members and veterans.