Trail Running calendar near Winchester 2026-2027

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.

Timed 5K and 10K trail run and walk at Red Wolf Sanctuary in Rising Sun, Indiana, with courses through waterways, wetlands and past wildlife enclosures and proceeds supporting the sanctuary's conservation work.

Experience Cincinnati longest running ultramarathon at the Stone Steps 50K and 27K Trail Run. Take on the wooded paths of Mt. Airy Forest in this historic event held just miles from downtown.

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.

A community Turkey Trot in Wendell Moore Park offering a 5 mile run and a 4K walk with chip timing, finish medals, and awards including overall male and female prizes.

Trail races at General Butler State Resort Park on 11/07/2026 include 5K, 10K, 13.1 mile, 20K relay and a 6 Hours of Power loop event with park facilities and river overlook.

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..

Trail running event in Red River Gorge, Slade KY on Nov 14, 2026 offering 30 km and 50 mile trail races; the course includes significant climbing and poles may be useful.

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.

A multiple distance trail running event in Hyden KY featuring a 100 mile backcountry loop plus 50k and half marathon courses over rugged terrain.

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 events on a 2-mile loop at Majestic Farm in Batavia, OH, featuring 48/24/12/8 hour options, a cupless format, free horse stalls, AWD divisions, and cash prizes for new 24- and 48-hour course records.

Timed ultraloop races and ruck events on a 5.4 mile loop in Parksville, Kentucky, with individual, relay, and ruck divisions. Full-service aid station, cup free policy, chip timing, and on site primitive camping.

A team 10K adventure race across a 575 acre Kentucky farm with 18 challenge checkpoints and a two hour time limit. A separate 1 mile community event offers food trucks, activities, and six open checkpoints.