Trail Running calendar near Pine Ridge 2026-2027

Experience a spring trail run through the wooded hills of Pulaski County Park along Lake Cumberland. Choose from half marathon, 10K, or 5K distances and earn a unique opossum finisher medal.

Experience the annual Union Half Marathon and Relay across two scenic trails in Big Stone Gap. Run through historic train tunnels on a USATF certified course while supporting local cross country and youth medical research.

Experience the inaugural Howlin' Wolfe 25k or 50k at Natural Bridge State Resort Park. Run through Red River Gorge on a mix of single track trails and fire roads while supporting local search and rescue teams.

Conquer a hilly road course or a family trail run at Wayne National Forest to support local cross country teams. This scenic event offers medals for top finishers and all participating children.

The ninth annual Fit Farmer 12K Trail Run takes place on the Flag Rock Area Trails in Norton. This event supports a local program that helps seniors access fresh food from the farmers market.

Experience a technical trail race in eastern Kentucky featuring a 10K or a Half Marathon. Navigate wooded terrain with significant elevation gains and fast descents at the scenic Perry County Park in Hazard.

Compete in the State Games of West Virginia at Heritage Farm with 11K and 5K trail races. This official qualifier offers runners the chance to earn a spot at the State Games of America while enjoying Appalachian scenery.

Explore Kentucky's trails at the Big Turtle Trail Runs. This untimed event in Morehead offers a 50K and a 10 Miler route on the scenic Sheltowee Trace. Finish by the cutoff to earn your finisher medal.

Test your endurance in the scenic forests of Norton Virginia with distances ranging from 25k to 100 miles. Conquer significant elevation gain to earn custom medals or legendary finisher buckles at the finish line.

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.

Run through the fields of Masterson Station Park in this cross country race featuring 5k and 10k distances. Enjoy a festive afterparty with bourbon tastings, music, and food trucks.

A 5K trail run on the Flag Rock Area Trails in Norton, VA, held as part of the High Knob Outdoor Fest. Proceeds support the festival and the event is hosted by the City of Norton and local partners.

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.

This 13.6-mile race starts at the High Knob Observation Tower in Virginia's Cumberland Mountains. The scenic route gains 1,600 feet on forest roads. Proceeds support local trail maintenance in Norton.

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..

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.

The Hellbender 10K is a 6.2-mile race that ascends over 2,000 feet to the summit of High Knob. This 13th annual event takes runners from downtown Norton to the highest point in the Cumberland Mountains.

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.

The Shawnee Trail Runs offer rugged wilderness adventures in Ohio's Shawnee State Forest. Choose from three distances, including a challenging 54-mile ultra with 11,000 feet of climbing. Experience remote, hand-maintained trails for a true..