Trail Running calendar near Winchester 2025-2026

The Cabernet Canter Cross Country 5K/10K is an annual running event held at Talon Winery in Lexington, Kentucky. Participants can choose between a 5K or 10K cross-country race through the scenic winery grounds. Each runner receives a race shirt and a Cabernet Canter wine glass, with a complimentary..

The GRC Cross Country Daniel Boone 5K Honoring a community member takes place in Winchester, Kentucky, on Saturday, August 30, 2025. This 5K offers a run or walk option for all ages. The course features a winding out-and-back route that starts at the corner of Lincoln Street and East Hickman Street..

Pride Run Lexington is a LGBTQ+-supporting running event produced by Frontrunners Lexington, held at Coldstream Park on the grounds of the Kentucky Horse Park in Lexington, Kentucky. The weekend event offers a 5K Run/Walk on scenic trails (chip-timed) and a 1 Mile Fun Walk, plus a volunteer option...

Run Baby Run 5K Benefiting NICU Babies is Lexington, Kentucky’s race held at Coldstream Park/Legacy Trail. The in-person 5K Run/Walk, a Kid’s Dash (1/4 mile) for children 10 and under, and a 5K Virtual Participant option make up the events. The flat, fast course follows the Legacy Trail through Cold..

Yeti Trail Run in Cincinnati, Ohio offers three off-road distances — 5K, 10K, and a half-marathon — run on trails through Mount Airy Forest and French Park. The course features wooded single-track, meadows, and a fossil-filled creek, with French Park providing the greatest elevation gain at about 33..

The Raven 10K is an annual trail running event held at Raven Run Nature Sanctuary near Lexington, Kentucky. This scenic 10K race takes place on the sanctuary's 734-acre grounds, featuring trails through meadows, woodlands, and streams, with historic early 19th-century settler remnants along the rout..

The General Butler Trail Race, held at General Butler State Resort Park in Carrollton, Kentucky, offers a variety of trail running events including a half marathon, 10K, 5K, 20K relay, and a unique 6 Hours of Power endurance challenge. The courses start and finish at the park's Recreation Center, fe..

The Rugged Red Trail Half Marathon is an annual trail running event held in Slade, Kentucky, at the scenic Red River Gorge. Celebrating its 11th year in 2025, the race features a challenging 13.1-mile loop on private trails, offering runners a unique and rugged outdoor experience. Participants recei..

6 Hours of Power at General Butler State Park (Recreation Center) in Carrollton, Kentucky, is a Wolf Pack Adventures endurance event. Runners complete as many 5K loops as possible within a 6-hour window, with a minimum four-loop finish to officially complete the race. The course is a single 5K loop..

The Forkland Festival Fox and Hound 4K is a unique trail running event held in Gravel Switch, Kentucky, within the scenic Forkland Community. This challenging 4-kilometer course features a steep quarter-mile uphill start, followed by open meadows and woodland trails, finishing with a downhill stretc..

Stone Steps 50K and 27K Trail Run takes place in Mt. Airy Forest, Cincinnati, Ohio, just a short distance from downtown. The event offers two trail ultramarathon distances: a 50K loop course and a 27K loop course on single-track trails through Mt.Airy’s 1,469.9-acre woods. Runners navigate a hilly,..

Pilgrimage in the Park is a Thanksgiving Day 5K Run/Walk at Pulaski Park in Nancy, Kentucky. The event offers a 5K Run/Walk and a Fun Run/Walk on scenic new trails, featuring views of Lake Cumberland. The 3.1-mile course is suitable for runners and walkers. A portion of the proceeds benefits the Ame..

The Run Empowered Series in Cincinnati, Ohio, is a dynamic multi-race challenge organized by Empower Ultras, designed to inspire runners to push their limits and celebrate achievements. Participants can choose from various distances and events throughout 2025, including 10Ks, marathons, ultra-distan..

The All Things Race P4v13 is a running event held in Corbin, Kentucky, at 578 Singing Hills Road. Scheduled for December 6, 2025, it features a 5K road run/walk, a 10K trail race, and a kids fun run. The race honors the legacy of Greg Deaton, a beloved pastor and camp director, and supports the Laur..

Topo Trail Marathon Races take place at East Fork State Park in Bethel, Ohio. The event offers three trail distances on a 6.55-mile lap: Quarter (one lap), Half (two laps), and Full Marathon (four laps), all on 100% singletrack mountain-bike trails. The course emphasizes tight, natural singletrack w..

Warbird 100 is a trail ultramarathon event held in Hyden, Kentucky. The race offers three distances: a 100-mile ultramarathon, a 50k, and a half marathon, inviting a range of runners to test endurance on rugged terrain around the Hyden area. A distinctive feature is the chance to witness many of the..