Trail Running calendar near Huddleston 2026-2027

Explore Wintergreen’s scenic Blue Ridge single track on a timed, non competitive trek with 7 to 28 mile options and 10 hours to finish. Enjoy rocky overlooks, a post trek party with food, finisher shirt and patches and medal opportunities.

Run the scenic Chessie Trail in Lexington, VA on November 7, 2026 with distances from 5K up to a USATF certified, Boston qualifying marathon. In person, virtual and four person relay options make it perfect for solo racers and teams alike.

Mountain Masochist Trail Run in Montebello VA features 100K, 50 mile and 50K courses through rugged Blue Ridge single track and forest roads at peak fall foliage. Finish at Montebello Campground with aid stations and a post race meal.

Join the DPS Education Foundation Turkey Trot in Danville this November for a scenic 5K run or walk along the Dan River and a family friendly kids fun run. Start and finish at American Legion Field while supporting scholarships and programs..