Trail Running Calendar Kentucky 2026-2027

Overnight running relays and ultramarathon events at Kroger Field in Lexington on July 18 to 19, 2026 raise funds for cancer patient support care. Options include marathon relays, a double marathon relay, a 12 hour ultra, and a survivors wa..

A cross-country 5k and 10k at Masterson Station Park on July 24, 2026, and the first race in a three-event series. Participants receive a race shirt, finisher award and a bourbon tasting ticket; under-21s do not receive tasting tickets.

A trail event at French Shelter Park in Cincinnati offering 5K, 10K and half marathon routes with notable elevation gain, themed 5K and 10K races, finisher medals, and a half marathon finisher t shirt.

A fundraising running event at Red Orchard Park in Shelbyville supporting The Dream Factory. Timed 3 hour, 6 hour and 12 hour events plus a 6 hour team relay take place on a two mile cross country course.

A charity 5K and virtual 5K at River Front Park in Brandenburg supporting an 11 year old boy with a serious brain injury; proceeds will help cover medical and out of pocket treatment expenses.

An obstacle and trail running event at Diamond Lake Resort in Owensboro, Kentucky, featuring 5K and 10K options, 28 obstacles, and youth races for ages 4 to 13. Proceeds benefit MentorKids Kentucky.

A two-day trail running and mountain bike weekend at McDougal Lake in Hodgenville, KY, featuring distances from 4 to 32 miles, junior and e-bike divisions, looped courses, and a Double Down multi-event option.

Trail runs in Iroquois Park with 7 mile and 4 mile options as part of the Kentucky Cryptid Series. Complete three of four races in-person or virtually to earn a Cryptid Series survivor medal and shirt.

A women only 5K obstacle mud run at Pop's Landing, Haddix Farms on August 16, 2026, featuring 18+ obstacles. Open to women aged 7 and older, the event emphasizes teamwork and a non-competitive atmosphere.

An evening of trail races at Pulaski County Park in Nancy, Kentucky, offering distances from 5K up to a 36K stage race, plus relay and combined-entry options. Registration windows and fees are listed for several events.

A 12 hour trail event at Saunder Springs Nature Preserve in Radcliff, Kentucky, offering solo, two person, and four person team options on a loop course that mixes technical and runnable trail with waterfalls and creekside sections.

A cross-country 5K and 10K at Talon Winery in Lexington with finisher awards and a wine drink ticket; under-21 participants receive the award but not the wine. The event includes wine sales, live music, and an after-party in the tasting roo..

Mud Happens, One Bad Mud Run is a three mile obstacle event at Phil Moore Park on August 29, 2026 that supports child abuse prevention. It offers competitive and non competitive heats, team entries, and a free kids mud 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.

Freedom 250 2.5K Trail Race at Pulaski County Park on August 29, 2026 features winding trails and rolling hills. The event acknowledges National Overdose Awareness Month and lists a $25 registration fee.

Experience a unique trail race through the historic Blackacre Nature Preserve featuring wooded paths and farm animal sightings. Choose between 4 or 8 mile distances and enjoy post race ice cream at the historic homestead.

GRC Cross Country Daniel Boone 5K is in Winchester, KY on September 5, 2026, with a down and back course from Lincoln and East Hickman to the country club. Entry fee is $30 and shirt registration is available until August 22.

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.

A community Pride Run at Coldstream Park on September 19, 2026 featuring a chip timed 5K with awards and a 1 mile fun walk. Proceeds support local LGBTQ+ school programs and related resources.

The Graves County 4-H Clover Classic will take place in Mayfield on Saturday 19 September 2026. You can run 5 kilometers.