Trail Running calendar near Winchester 2026-2027

A 5K style mud and obstacle course in East Fork State Park featuring more than 15 natural and man made obstacles, from crawls and climbs to cargo nets and a final sandy beach run. The route uses existing trails and is about 3.1 miles.

A trail race at French Shelter Park in Cincinnati offering 5K, 10K and a 13.1 mile half marathon on meadow and woodland trails with notable elevation gain and finisher medals.

A trail race day at Green River Lake State Park on May 30, 2026 featuring a kids 0.8 mile run, a 5K, a more technical 10K, and a new half marathon; bib pickup is Friday in downtown Campbellsville and race morning at the venue.

Big Turtle Trail Runs returns to Morehead, Kentucky on June 6, 2026 with two trail races, a 50K and a 10 Miler. Registration runs March 1 to April 30 with fees of $75 and $35.

A June 20 nature run at Loretto Motherhouse offering 5K, 10K and a virtual 5K. The course goes through woodlands, lakes and grassy trails, walkers are welcome and proceeds support the Loretto Community.

Experience a 3.6 mile trail run at French Park featuring meadows and multiple creek crossings. This fourth leg of the Dirt Days Trail Series offers age graded awards and random door prizes in a picturesque Cincinnati park.

Experience private trails and spectacular arch views at The Ascent in the Red River Gorge. Choose between the 5K and 10K distances for a rewarding trail event featuring significant climbs and professional timing.

A 30K trail race at Mount Airy Forest in Cincinnati made of three 10K loops. Finishers receive a t-shirt and medal; the race counts toward the Alpine Trail Race Series and awards series points.

An overnight relay event at Kroger Field in Lexington offering marathon, double marathon and 12 hour ultra relay options. Proceeds support cancer patient care and the event is cupless, so participants should bring their own cup.

Evening cross country races of 5k and 10k at Masterson Station Park on July 24, 2026, with music, food trucks and bourbon tastings. The 5k allows walkers and the 10k has a 16 minutes per mile cutoff.

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.

Run For Dreams in Shelbyville offers 12 hour, 6 hour and 3 hour individual timed races plus a 6 hour team relay to benefit The Dream Factory. The course is a two mile cross country loop at Red Orchard Park and food will be available.

Experience the original event of the Dirt Days Trail Series at East Fork State Park. Run through densely wooded trails on a 5.6 mile or 10.8 mile course with options for early starts and various participation categories.

A women only 5K obstacle mud run in Glencoe, Kentucky on August 16, 2026, featuring 18 plus obstacles and open to participants aged 7 and older. The event is non competitive and allows running, jogging, or walking.

Experience a cross country race through the scenic grounds of Talon Winery in Lexington. Enjoy a finisher award plus a glass of wine and live music at the post race celebration.

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.

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.

Trail ultras at East Fork State Park near Bethel, OH, offering 100 mile, 100K, 50K and 15 mile courses on a roughly 33 mile loop around William H. Harsha Lake. The cupless event uses manned and unmanned aid stations, cutoffs, required gear,..

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 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.