Trail Running calendar near Pine Ridge 2025-2026

Run the Dirty Dog Trail 4 Miler on November 8, 2025 at Veterans Park in Lexington. Scenic and technical 4 mile trails with roots, rocks and creek crossings, offered in person or virtual. Proceeds support Hickman Creek Conservancy.

Take on the Black Gold Endurance Challenge at Belfry High School with 24 hour or 12 hour timed laps on a mostly flat one mile loop. Run solo or as a three person relay for a unique overnight test of grit and strategy.

Run or stroll a new 5K at Kentucky Horse Park, finishing inside a festive Holiday Village with lights, Santa photos and mini train rides. Choose chip timed competitive entry or a relaxed untimed stroll, family and dog friendly.

Join the Pilgrimage in the Park 5K Run/Walk on Thanksgiving Day at Pulaski Park in Nancy, Kentucky, for a scenic trail run with views of Lake Cumberland. Proceeds support the American Cancer Society and a fun family run welcomes everyone.

Join a festive 5K road run or walk, 10K trail race, and kids fun run on Dec 6 in Corbin to honor a beloved pastor and support Laurel Lake Baptist Camp. Enjoy holiday decorations, hot cocoa, cookies and family friendly fun.

Run the Frozen Nuts Trail Run in Nancy, Kentucky on January 3, 2026 with a half marathon, 10K, 5K and a 5K competitive walk. Scenic winter trails and solid on course support make it great for racers and casual runners alike.

Challenge yourself at Conquer The Wall in Williamson WV, a 47 or 35 hour ultrarun on a flat 2.05 mile paved loop along the flood wall. Run solo or on a team and earn finisher gear and belt buckles at 50 and 100 miles.

Run the wild Warbird 100 in Hyden, Kentucky this mid March 2026, with 100 mile, 50k and half marathon options on scenic trail terrain. Shorter course runners may meet 100 mile finishers as routes overlap near the finish.

Hit the trails in Nancy Kentucky on March 21 2026 for the Lucky Opossum, featuring a half marathon, 10K, 5K run and a 5K competitive walk. Scenic singletrack and friendly competition make it a perfect spring challenge.

Take on the Southern Grit Endurance Challenge in Parksville KY April 18 and 19 2026 with timed 3 Hour to 24 Hour running and rucking on a scenic loop where wooded hills meet farmland. Camp onsite, race into the night with required headlamps..

Join the Fit Farmer 12K Trail Run on May 23, 2026 in Norton, Virginia, over scenic Flag Rock Area Trails from the Norton Reservoir Trailhead. Run for fresh air and community as proceeds support the Norton Farmers Market Senior Supplement pr..

Hilly 5K trail run or walk through Red River Gorge on June 27, 2026, starting at Natural Bridge Campground in Slade, KY. See rock arch views, snag a tie dye shirt while supplies last, and enjoy awards, photos, food and music.

Run scenic trails at the Flag Rock 5K in Norton, Virginia on August 13, 2026. Part of the High Knob Outdoor Fest, this lively 5K supports the festival and showcases the Flag Rock Recreation Area.

Experience a scenic 13.6 mile half marathon around the Mountain Fork watershed, finishing with a climb to High Knob Observation Tower near Norton Virginia. All proceeds support trail development and maintenance on Flag Rock and High Knob.

Join the Run Baby Run 5K in Lexington for a flat, family friendly course through Coldstream Park that supports NICU families. Enjoy a kids dash, commemorative tee and virtual option while helping provide essentials for babies in need.

Experience the Raven 10K through scenic trails at Raven Run Nature Sanctuary in Lexington on Sunday, September 27, 2026. Limited to 170 runners, this 12th annual trail race features performance shirts and custom age group medals.

Tackle the Hellbender 10K in Norton, Virginia on October 3, 2026, a challenging uphill 6.2 mile run that gains over 2,000 feet to the High Knob summit. Join fellow runners for the 13th annual climb and spectacular mountain views.

Run a scenic but rugged 13.1 mile trail through Red River Gorge from Natural Bridge Campground, with finisher medal, shirt, postrace BBQ and beer for 21 plus. Proceeds support local Search and Rescue teams.