Perched at the spectacular confluence of the Potomac and Shenandoah Rivers where Maryland, Virginia, and West Virginia meet, this town is a geographical masterpiece that has been a flashpoint for American history for over two centuries.

Shepherdstown, West Virginia, holds the title of the oldest town in the state (chartered in 1762), and its Old Town District is a remarkably well-preserved slice of 18th and 19th-century Americana. Walking through it feels less like a museum and more like a living, breathing community that just happens to have stunning architecture.

While Shepherdstown is the "cool older sister" with its university vibe and river views, Charles Town is the stately, historic soul of the county. Founded in 1786 by Charles Washington (George’s youngest brother), the town was designed with a sense of destiny—quite literally, as Charles named the streets after his family members.