Trail Days Info – Appalachian Trail Days is an annual festival held in the small town of Damascus, Virginia. The Appalachian Trail runs from Georgia, to Maine. Damascus, Virginia is roughly the halfway point, it is notable for that as well as the fact that Damascus is the only town that the Appalachian Trail actually passes through. The sidewalk on Main Street in Damascus is actually part of the Appalachian Trail. Trail Days is a celebration of the Appalachian Trail and it’s people. The few who have hiked the entire trail, the few who help maintain and preserve the trail, the many who have hiked part of the trail, and anyone who enjoys being outdoors. Trail Days is a chance for them to celebrate.