Kentucky
Kentucky Trail Running Calendar 2026-2027
Explore the best trail runs in Kentucky for 2026-2027! Our updated list features 55 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
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.
Experience scenic overlooks and wooded trails at Iroquois Park with 7 mile and 3.4 mile road races featuring finisher medals and views of downtown Louisville.
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 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 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.
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 race across the Lake Barkley and Kentucky Lake bridges with two- and three-person relay options through Land Between the Lakes.
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.