Kentucky
Kentucky Trail Running Calendar 2026-2027
Explore the best trail runs in Kentucky for 2026-2027! Our updated list features 54 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 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 with 18+ obstacles at Pop's Landing in Glencoe KY on September 6, 2026; open to participants aged 7 and up who can run, jog or walk.
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.
Community 5K and 1-mile fun walk in Berea on September 20, 2026, with chip timing, commemorative shirts and a virtual 5K option.
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.
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 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.
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 5K trail run in Forkland on October 10, 2026, across hills, meadows and woods; registration includes a pancake breakfast ticket and a T-shirt.
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.