Trail Running calendar near Winchester 2026-2027

A team event on May 16, 2026 featuring a two-hour *10K* course across a 575-acre Versailles farm with 18 checkpoints including mountain biking, ziplining, archery and canoeing. Teams compete in male, female and mixed divisions.

Experience the ridges and meadows of Mt. Airy Forest in this multi distance trail race. Choose between 5.4 or 10.6 miles with early start options for those needing extra time on the scenic counter clockwise loop.

Experience a technical trail race in eastern Kentucky featuring a 10K or a Half Marathon. Navigate wooded terrain with significant elevation gains and fast descents at the scenic Perry County Park in Hazard.

Approximate 5K adventure race at East Fork State Park near Cincinnati with 15+ natural and man-made obstacles, from mud crawls and wall climbs to cargo nets and a sandy beach finish.

A 13.1 mile trail race at French Shelter Park in Cincinnati on May 30, 2026, run as four 5K loops plus a 1K loop. The route passes meadows, wooded trails and a creek and includes about 331 ft of total ascent.

Experience the natural beauty of Green River Lake State Park with several trail distances ranging from a kids run to a half marathon. Join this off road event in Campbellsville for a day of technical climbs and scenic park trails.

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.

Hilly trail races in Red River Gorge offering a 5K and a new 10K on private property. Events start and finish at Natural Bridge Campground and include commemorative shirts, medals, on course water and free race photos.

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.

A multi-sport relay event at Kroger Field in Lexington that raises funds through TeamRaising and donations to help cancer patients with needs such as gas, hotels, and meals.

A 50k at Creekside Center, Beckley Creek Park, run as four laps on an 8-mile loop mixing technical single-track and paved stretches. Runners join one of two teams and may run a single lap as a pacer or the full distance to help their team.

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.