Trail Running calendar near Pine Ridge 2025-2026

Join the Frozen Nuts Trail Run in Nancy, KY on January 3, 2026 for a scenic winter day of trail running with a half marathon, 10K, 5K run or 5K competitive walk. Choose your distance and enjoy trails, camaraderie, and cool weather racing.

Challenge yourself at the Warbird 100 in Hyden, Kentucky, a race weekend offering 100 mile, 50k and half marathon options. Shorter runners soak up the energy as many 100 mile runners finish, making for a festive finish.

Hit the trails at Lucky O'possum in Nancy, KY on March 21, 2026, with 5K, 10K and half marathon options for every pace. Expect rolling singletrack, friendly competition and postrun smiles for runners of all levels.

Union Half Marathon & Relay on April 11 in Big Stone Gap: scenic trails, tunnel passages, and options for relay or virtual runners. Finishers get a medal and shirt.

Run the Fit Farmer 12K in Norton VA along the scenic Flag Rock Area Trails. Proceeds support the Norton farmers market senior supplement program that helps low income seniors buy fresh local produce.

Test your limits at the Woodbooger 100 in Norton, Virginia on June 13 and 14 2026, with scenic trails, big elevation and lively local support. Choose from 100 mile, 100 km, 50 km or 25 km and chase a finisher buckle or custom medal.

Run the Ascent Red River Gorge 5K on June 27, 2026 at Natural Bridge Campground in Slade KY, a scenic trail with rewarding climbs and views of natural arches. Celebrate at the finish with music, food and tie dye shirts while supplies last.

Join the Flag Rock 5K Trail Run in Norton VA on August 13, 2026 for a scenic run through the Flag Rock Recreation Area trails. Part of the High Knob Outdoor Fest, this community event benefits the festival and celebrates outdoor adventure.

Run the rolling grounds of Talon Winery at the eighth annual Cabernet Canter, with scenic 5K and 10K cross country courses. Enjoy finisher awards, a wine ticket and live music while celebrating among the vines.

Run a scenic 13.6 mile loop from High Knob Observation Tower near Norton Virginia, climbing through forest roads with sweeping mountain views. Proceeds support trail maintenance and all finishers earn medals.

Join the Spoonbread Festival 5K in Berea, Kentucky on September 20 for a friendly flat and fast run or a relaxed 1 mile fun walk along the scenic Berea City Trail. Enjoy chip timing, commemorative shirts, music, food and a water stop while..

Run Baby Run 5K returns to Lexington's Coldstream Park and Legacy Trail with a flat, fast course and a Kid's Dash for young runners. All proceeds support the Snow Bunny Baby Project to buy diapers and wipes for NICU families.

Join the Raven 10K on Sunday, September 27, 2026 for a scenic trail run through Raven Run Nature Sanctuary near Lexington, KY. Choose in person or virtual entry and tackle a challenging 10K in a beautiful park setting with limited field.

Take on the Hellbender 10K on October 3, 2026 in Norton, Virginia, a scenic yet relentless climb from downtown to the High Knob summit. Now in its 13th year, this uphill test gains over 2,000 feet and rewards runners with sweeping summit vi..

Experience the Rugged Red Trail Half Marathon in Red River Gorge on October 3, 2026. Tackle 13.1 miles on site or virtually, earn a long sleeve shirt and finisher medal, enjoy BBQ and beer, and support local search and rescue.

Join the Thunderbunny Trail Races at Strouds Run State Park on May 9, 2026, with 50K, 25K and 11K options across scenic singletrack. Enjoy a well organized day of challenging trails and community spirit for runners of many levels.