Trail Running calendar near Winchester 2026-2027

Experience a women only 5K obstacle mud run at Pop's Landing at Haddix Farms. Join a community focused on unity and empowerment while tackling a fun mud course to support breast cancer awareness.

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.

Run the Deer Trail Run Half-Marathon through the scenic trails of Cincinnati's Mt. Airy Forest. This themed trail event awards series points and finisher medals. Costumes are encouraged for a chance to win an award.

Looped trail ultramarathons and a 15 mile out and back at East Fork State Park around William H. Harsha Lake, with single track, creek crossings, aid stations, cupless rules, mandatory gear, pacer options, and set cutoffs.

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.

Join the 30th annual Spoonbread Festival 5K in historic Berea. Run or walk a flat, paved course on the city trail, with festivities supporting the local chamber of commerce. Enjoy chip timing, a race shirt, and the vibrant atmosphere of the..

Run, walk, or volunteer at the Run Baby Run 5K to support NICU babies. This flat course on Lexington's scenic Legacy Trail includes a kids' dash and virtual options. All proceeds purchase supplies for families in neonatal intensive care uni..

Hit the trails at the Yeti Trail Run in Mount Airy Forest Cincinnati with 5K, 10K, half marathon and 30K options through meadows, woods and along a fossil creek. Finishers get medals, costumes are encouraged and walkers are welcome.

Experience the natural beauty of Lexington at the Raven 10K Trail Run. Run or walk through grassy fields and primitive trails at the Raven Run Nature Sanctuary or join the event virtually from any location.

Experience a scenic trail run through the Red River Gorge on a private looping course. This cup less half marathon supports local search and rescue teams while offering a festive atmosphere with medals and post race meals.

Shawnee Trail Runs near West Portsmouth, OH features 54 mile, 50K and 13.1 mile courses with substantial elevation gain and long remote sections. The 54 mile route includes a nine mile "Dark Side" through a hand maintained wilderness area.

Honor history at the Mogadishu Mile, a four person team obstacle course and one mile ruck run in Georgetown. Work together to complete 500 total reps and a weighted run without leaving any team member behind.

Experience a unique trail run through the hills and woodlands of Gravel Switch. Enjoy a route featuring meadows and steep climbs followed by a pancake breakfast and handmade awards at the local heritage festival.

The Little Rooster Run offers a weekend of trail events in Glencoe, Kentucky, from a kids' fun run to a 5K and the unique Mini Barnyard Ultra. This "last runner standing" format challenges participants on a 2-mile loop every half hour. Proc..

Join the second annual Running Pumpkin 5K in Lexington's Coldstream Park. This fall event supports Gleaning Housing, a local nonprofit building affordable rental homes. Participants are welcome to bring a pumpkin or wear a costume, with sna..

Experience Cincinnati's longest running ultra marathon through the scenic single track trails of Mt. Airy Forest. Choose between a 50K or 27K loop course featuring technical terrain and significant elevation changes.

Little Batty Trail Runs on 10/25/2026 in Nancy, KY features trail courses of 13.1 miles, 10K and 5K with creek or dry lake bed crossings, cross country sections and a short pavement segment; registration runs 3/20 to 8/31/2026.

Experience a themed trail run through Cincinnati's French Shelter Park with options for a 5k or 10k distance. Participants enjoy costume contests and holiday activities while earning points toward a global series award.

Turkey Trails Cincinnati presents in-person and virtual running options on 11/14/2026 in Hamilton OH, from a 50 m kids dash up to a half marathon. Event features include chip timing, shirts, custom bibs, medals, free photos, and finish-line..

Celebrate Thanksgiving at Pulaski Park with a scenic trail run overlooking Lake Cumberland. Choose between a 5K or a Fun Run while supporting the American Cancer Society and enjoying views of the water.