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!
August 2026
Eighth annual Cabernet Canter Cross Country at Talon Winery features 5K and 10K races, finisher awards with a wine ticket, plus live music and an after-party.
A muddy 3 mile obstacle run at Phil Moore Park on August 29, 2026, with 20 or more obstacles and a free kids play area.
Trail races at Mt. Airy Forest in Cincinnati include 5K, 10K, a 13.1 Miles half marathon and 30K. Finishers get medals, half marathon and 30K include shirts, and the event awards series points across the ATR season.
A 2.5K trail race on August 29, 2026 at Pulaski County Park in Kentucky that recognizes National Overdose Awareness Month and offers a clearly marked course with professional timing.
Trail races of 4 miles and 8 miles at Blackacre Nature Preserve with farm animals on course, finisher medals, awards, and a cupless water policy.
September 2026
A community 5K run or walk in Winchester, KY with a winding out-and-back course, event shirts for early registrants, and proceeds supporting the GRC Cross Country team.
A free cross country 5K in Georgetown KY with on-site shirt printing, concessions, and proceeds supporting a local running team's registration fees.
Women only 5K obstacle mud run at Pop's Landing in Glencoe, KY with 18 plus obstacles, open to ages 7 and up and focused on teamwork and shared experience.
An illuminated night run and walk at Glenwood Gardens with marked trails, a two-loop 3.26 mile run and a one-loop 2 mile walk; the run counts toward Dirt Days Trail Series points and online registration is required.
Community Pride Run at Coldstream Park with a chip timed 5K, 1 mile walk, virtual option, music and vendor tables supporting LGBTQ+ students and families.
The 30th annual Spoonbread Festival 5K in Berea KY offers a chip timed 5K on a flat paved trail, an untimed 1 mile fun walk, and a virtual 5K option with commemorative shirts and age group awards.
Trail and park runs starting and finishing at the Iroquois Park amphitheater, offering 7.5 miles and a 3.4 mile Short Loop with medals for finishers.
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 on a 0.31 mile concourse loop with individual and four person relay options, 24 hour aid station, shirts, medals, and a 100 mile buckle.
A 30K trail race in Cincinnati run as three laps of a 10K loop, featuring meadows, wooded trails and notable elevation gain. Finishers receive a medal and 30K entrants receive a finisher t-shirt; walkers are welcome.
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.
Experience the natural beauty of Lexington at the Raven 10K Trail Run. Run or walk through grassy fields and primitive trails at the Raven Run Nature Sanctuary or join the event virtually from any location.
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.
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.
A free annual military fitness tribute at Queenslake Horse Farm honoring the 19 soldiers lost in the 1993 Battle of Mogadishu, featuring a memorial course and a full day music festival.