Shepherdstown West Virginia is where I currently attend Shepherd University so I am very familiar with the town. The whole area has a lot of historical sites and is located close to Harpers Ferry. If you are located in the DC metro area I would recommend getting lunch in town for a day ride. My favorite restaurants are The Blue Moon and Mellow Moods, if you aren’t hungry there are a number of good cafes in town. Parking can be an issue but parking a bike is always easier than a car or truck.