Trail Running calendar near Winchester 2026-2027

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.

A strategy-driven trail event at Paintsville Lake State Park where a marked half marathon course includes ten optional off-trail checkpoints with time bonuses. Two checkpoints are drawn mandatory at the start and skipping them creates penal..

The Zenith Adventure Trek will take place in Pine Ridge on Saturday 11 July 2026. You can run 20 miles.

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.

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.

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.

Muddy Princess Kentucky is a 5K obstacle mud run in Glencoe on August 16, 2026, offering standard, VIP and volunteer options and supporting the National Breast Cancer Foundation with on site photos, hydration points and a rinse off station.

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..

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.

A 2.5K trail race at Pulaski County Park on August 29, 2026, with a well-marked course and professional timing. The event also recognizes National Overdose Awareness Day and highlights local outdoor scenery.

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 adventure race at East Fork State Park where solo competitors or teams trek, bike, and paddle to collect checkpoints using map and compass. Timed 6 hour and 12 hour formats are USARA sanctioned and include boat rental options.

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.

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.