The Wilderness Road

12. Wayside Inn

Winchester, VA

In operation since 1797, The Wayside Inn is reportedly America's longest running inn. Originally known as Wilkenson's Tavern, travelers stopped here for food and rest as they travelled through the valley. Later the tavern became a stagecoach stop. Today the inn is filled with rare antiques and an extensive Americana collection that offers visitors an opportunity to step-back in time.