In 1634, under the direction of King Charles I, the Virginia House of Burgesses divided the colony into eight original shires. Accomac Shire was one of them, the easternmost, taking in the whole of Virginia's Delmarva territory. In 1642 the name was anglicized to Northampton County. In 1663 Northampton was split into two; the northern two-thirds reclaimed the original Accomack name, and the southern third kept Northampton. The two counties have stayed that way ever since, the only counties in Virginia that lie on the Delmarva Peninsula. As of the 2020 census, 45,695 people lived between them. It is, by a substantial margin, the least populated part of coastal Virginia.

The land is flat in the way only a coastal plain can be flat. From the sand of the barrier beaches in the east to the bay marshes in the west, the elevation rarely exceeds fifty feet above sea level. The soil is sandy and deep, ideal for the cotton, soybeans, vegetables, and truck farms that have anchored the local economy for two centuries. Large-scale chicken processing came later, with Perdue and Tyson now operating big plants on the Shore. The weather is moderated by water in every direction; the bay tempers the cold winters, the Atlantic tempers the hot summers. The historian William G. Thomas called this place "a liminal place, a zone of interpenetration, where the settlement patterns, speech, demography, and political outcomes defined its place in the South but its engagement with technology and rapid transformation of the landscape betrayed other allegiances."

Two pieces of infrastructure shaped the modern Eastern Shore. The first was the New York, Philadelphia and Norfolk Railroad, built down the spine of the Delmarva Peninsula in the late 1880s and terminating at Cape Charles. It brought wealthy northern sportsmen to the barrier islands, hauled produce to Philadelphia and New York, and made the Shore briefly prosperous. Passenger service ended in 1958, and the rails are now mostly gone or repurposed. The second piece was the Chesapeake Bay Bridge-Tunnel, opened in 1964: seventeen and a half miles of trestle, low bridges, man-made islands, and twin underwater tunnels carrying U.S. Route 13 across the mouth of the bay. Before the tunnel, you reached the Shore by ferry from Little Creek to Cape Charles. After the tunnel, you reached it by car in twenty minutes, and the rest of Virginia became theoretically closer, though the Shore stayed stubbornly itself.

Three small airports dot the Shore. Accomack County Airport at Melfa is the largest, with a paved runway used by general aviation and the occasional medical flight. Campbell Field is a turf strip at Weirwood. Tangier Island has its own airport on the small fishing community in the middle of the bay. STAR Transit runs the buses, two counties' worth of fixed routes and paratransit. The Eastern Shore Post and Eastern Shore First serve as the local press; WESR-AM and WESR-FM cover the radio. The politics break along county lines, with Accomack leaning Republican and Northampton leaning Democratic, and the combined Shore tilts Republican by the larger Accomack population. In the 2025 gubernatorial election the Shore voted against the Democrat Abigail Spanberger even as Spanberger won the state by fifteen points. The Shore has always been Virginia, but Virginia has always been somewhere else.