Trail Running calendar near Winston-Salem 2025-2026

Run scenic trails at Grayson Highlands State Park on courses from 8 to 50 miles with big climbs and amazing views. Proceeds help the park and local rescue and every finisher gets headwear, a medal, post race food and free pro photos.

Experience the Moonlight Bootlegger, a night trail 5K at Hagan Stone Park marked by hundreds of LED tea lights and live bluegrass. Bring a headlamp and enjoy a race shirt, commemorative mason jar and post race cocktails.

Run scenic trails at The Mighty Mountain Run 5K and 10K in Sophia North Carolina on May 9, 2026, a fundraiser for camper scholarships at Camp Caraway. Expect rugged single track, rewarding climbs, medals and pro chip timing.

Run on private Monroe farmland: a 4.167 mile Back Yard Ultra loop each hour until one runner remains, or a single 4.167 mile Celebrity Fun Run for walkers and joggers. Expect intermediate trails, self supported laps, village camping and mus..

Wicked Root 50K in Lowell NC on June 13, 2026 offers a tough 50K and a fun 5K on rugged 10 mile loops with big climbs and well stocked aid stations. Finishers receive unique handcrafted medals from BlueGill Pottery.

Run 100 or 50 miles on a challenging one mile loop with about 500 feet of climb per lap at Froggy Mountain in Galax, Virginia on June 19, 2026. Aid stations, hot food, toilets and outdoor hot showers are provided and a 60 hour cutoff lets y..

Celebrate the 40th Ultimate Runner in Winston Salem on June 27, 2026, a single evening challenge of four track races plus a 5K cross country. Complete all five events to earn a finishing score, commemorative shirt, and car decal.

Test your limits on looped, technical trails at Crystal Springs Recreation Area with 12 hour, 6 hour and 3 hour timed options that wind through High Rocks and Boundary trails. Shuttle service is required and this is a cupless event so bring..

Hit twisty trails and climbs at Black Copperhead Sting in Belmont NC on August 15, 2026, with 50K, 25K or 5K loop options. Aid stations offer savory and sweet fuel and finishers earn a one of a kind handmade pottery medal.

Run day or night at Hagan Stone Park in Carpe Diem Carpe Noctem, a Half Marathon and 10K on smooth marked trails with a moodier evening option. Complete both to link medals and take home a custom hoodie with post race food and photos.

Join the Donate Life NC Hero Run in Durham on Sept 13 for a family friendly 5K, 1 mile fun run or Sleep In Superhero option along the scenic American Tobacco Trail. Proceeds support organ, eye and tissue donation outreach.

Hit the scenic trails in Wilkesboro at the Chad Lovette Memorial Trail Run, with 5K and 10K timed options plus a 5K walk and virtual choice. Race in September to support the American Cancer Society and Relay for Life.

Run the scenic New River Trail in Max Meadows VA, with river views, trestle crossings and a mostly flat gravel trail. Choose 50 or 100 miles with aid, crew access and a buckle for 100 mile finishers.

Run rustic trails on a 50 acre horse ranch at Bit of Hope Ranch on Saturday October 10, with a certified 5K, a 2K walk, and a Half Pint kids run. A virtual 5K option welcomes every pace and family fun.

Run the Triple Lakes Trail Race at Bur Mil Park, weaving scenic trails around Lake Brandt, Lake Townsend and Lake Jeanette. Choose marathon, half, 40 mile, relay, ruck or virtual entries and earn a custom finisher medal.

Take a chance at The Unforeseen, a dice determined trail race at Reedy Creek Nature Preserve on November 14. Loop the scenic 2.25 mile course until fate calls it quits, enjoy free photos and compete for a Damascus steel knife.

Celebrate Thanksgiving weekend on trails at Cane Creek Mountains with the Black Toenail Friday Half Marathon and 7.5 Mile. On site and virtual options, finishers gear and post race food await on scenic singletrack.