Great Small Towns Near DC: Shepherdstown

Pedal and paddle through one of the oldest (yet lively!) towns in West Virginia.

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.

A beer at the Mecklenburg Inn is a nice way to wind down after a day of biking and paddling through Shepherdstown. Photograph by Lexey Swall.

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.

Population: 2,095.

Distance from DC: 71 miles.

Don’t miss: The Contemporary American Theater Festival, which stages mostly original plays in repertory.