Trail Running calendar near Winchester 2026-2027

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.

A 30K trail race in Cincinnati run as three laps of a 10K loop, featuring meadows, wooded trails and notable elevation gain. Finishers receive a medal and 30K entrants receive a finisher t-shirt; 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.

Trail races in Shawnee State Forest near West Portsmouth, Ohio, offering a 54 mile route with 11,000 feet of climbing, a 50K with 6,500 feet, and a 13.1 mile option added in 2023 that includes notable hills and runnable trail sections.

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.

A weekend of races at the Gallatin County Fairgrounds in Glencoe, Kentucky featuring an 800 m kids run, a 5K trail with a two hour cut off, and a last runner standing ultra run on repeated 2.083 mile laps. Headlamps required for the ultra.

A second-annual fall 5K hosted by Gleaning Housing at Coldstream Park / Legacy Trail in Lexington, KY, with pumpkins for donors and snacks and drinks for all participants. Participants may bring or wear a pumpkin costume.

Trail races in Mt. Airy Forest near Cincinnati offering a 50K ultra and a 27K loop course across single-track, hilly trails with aid stations, timing chips, and proceeds supporting local parks.

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..

A *4 miles* trail run and walk at Veterans Park in Lexington on November 14, 2026, over mostly hard-packed dirt trails with grassy and short paved sections. The race is chip timed, offers awards, hydration stops, and a virtual option with m..

A Thanksgiving trail event at Pulaski Park in Nancy, Kentucky on November 26, 2026 featuring a 5K and a 1 mile fun run with proceeds benefiting the American Cancer Society and awards for overall, age group, and team divisions.

Trail races at East Fork State Park on December 6, 2026, using a 6.55 mile singletrack loop with Quarter, Half, and Full options, on-course aid stations, chip timing, race shirt if registered by 11/14, and a finisher medal for all finishers..

Trail races at Pulaski County Park on Lake Cumberland, featuring a 13.1 mile half marathon, a 10K and a 5K. Trails are well marked and include rolling hills plus a notable finisher hill.

Trail event in Hyden, KY on March 19 and 20, 2027, featuring 100 mile, 50k and half marathon courses. The 50k ties into the 100 mile route and route files are available from the organizer.

Trail events in the Red River Gorge on March 27, 2027 offering 25K and 50K courses from Natural Bridge State Resort Park with mixed road and single track terrain, aid stations, and a 200-runner field cap.

Timed trail event at Majestic Farm with 2-mile loops, cupless aid, free horse stalls, AWD and rucking options, and multiple timed distances including 48, 24, 12, and 8 hour formats.