Some railways retire. The Virginia Creeper Trail simply changed gears. Stretching 34.3 miles through southwest Virginia, this trail follows a former rail line once used to haul lumber and iron ore through the Appalachian Mountains. Its unusual name traces back to the steam locomotives that labored up steep grades in the early 1900s.

Centered around Damascus, known as 'Trail Town USA,' the trail is famous for its 47 wooden trestles, sweeping mountain views, and outdoor adventures. Damascus is also one of the few places where the Appalachian Trail passes directly through a town's Main Street.

One of the trail's highlights is a 17-mile downhill ride from Whitetop Station, the route's highest point at 3,500 feet, to Damascus. Riders can coast nearly 1,600 feet downhill with little pedaling. Another standout feature is the High Trestle, a 550-foot bridge that rises 100 feet above the valley below. Following damage from Hurricane Helene in 2024, the upper section remains closed for restoration, while the Damascus-to-Abingdon section continues to stay open.