24 Small Town Escapes in America Perfect for a Relaxing Retirement

5. Shepherdstown, West Virginia – A History Lover’s Dream

The oldest town in West Virginia, Shepherdstown is a picturesque, history-rich destination with a vibrant, welcoming community. Located along the Potomac River, it blends small-town charm with a progressive, artsy vibe, thanks to Shepherd University. Bookshops, cafés, and music venues line its charming streets, while nearby trails and parks make it a great spot for active retirees.