Established in 1762, Shepherdstown is one of the oldest towns in West Virginia, yet it feels youthful—students from Shepherd University help energize the community. Just a five-minute stroll from the historic downtown deposits you on the banks of the Potomac River. You can walk or bike the C&O Canal Towpath, row down the river on a kayak from Pedal & Paddle, or choose a relaxing float trip past the famed battlefields on Antietam Creek with River & Trail Outfitters in nearby Knoxville.
Afterward, head to German Street, Shepherdstown’s main thoroughfare, for indie shops such as German Street Coffee & Candlery, a gourmet market with local jams, chocolates, wine, and other edibles. Cool off with a smoothie at Mellow Moods Café (119 W. German St.; 304-876-0608) or try a burger at Mecklenburg Inn (128 E. German St.; 304-876-2126), an English pub with a charming beer garden.
Distance from DC: 71 miles.
Don’t miss: The Contemporary American Theater Festival, which stages mostly original plays in repertory.