Kentucky
Kentucky Trail Running Calendar 2026-2027
Explore the best trail runs in Kentucky for 2026-2027! Our updated list features 82 exciting trail runs across the region. Find your next trail run in Kentucky below and join the trail community at these great events!
September 2026
A charity 5K at Coldstream Park/Legacy Trail in Lexington on September 26, 2026 benefits NICU babies, with an in-person chip timed 5K, a kids 1/4 mile dash, and a virtual 5K option with mailed shirts.
A 24 hour stadium ultra at Bowling Green Hot Rods Stadium where runners complete a .31 mile loop to log as many laps as possible; relay teams of four welcome.
Medal Madness in Bowling Green, KY on 09/26/2026 offers 5K, 10K, and a half marathon with finisher medals and published results; note limited onsite staff, no EMS stationed, and restricted water stations.
A 30K trail race at Mt. Airy Forest in Cincinnati run as three 10K loops, with a finisher t-shirt, medal, ATR series points, and a five-hour course limit.
A 3.1 miles light trail 5K at Elizabethtown Nature Park on September 26, 2026, with age group awards; adult registration is $25 and kids 12 and under run free.
A limited-field trail 10K at Raven Run Nature Sanctuary with a virtual option, commemorative shirts, and awards for top overall and age-group finishers.
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.
A 13.1 Miles trail half marathon in the Red River Gorge with in person and virtual options, age-group awards, commemorative shirt and medal.
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.
An exclusive nighttime 2.6 mile run in downtown Cincinnati offering early access to select BLINK installations and an interactive art experience.
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 at Thomas Nelson High School on October 17, 2026 supporting the Nelson County Schools UP Foundation and the Imagination Library.
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.