[1] Accomac Shire was established in the Virginia Colony by the House of Burgesses in 1634 under the direction of King Charles I.

The weather in the area has temperate summers and winters, significantly affected by the Chesapeake Bay and the Atlantic Ocean.

[6] Since the late 20th century, vineyards have been developed in both counties, and the Eastern Shore has received recognition as an American Viticultural Area (AVA).

At the northern end of the Atlantic side is the beach community of Chincoteague, famous for its annual wild pony roundup, gathered from Assateague Island.

The town of Wachapreague on the Atlantic coast is a popular destination for fishing and guided trips out to the wild barrier islands.

[7] Geographically removed from the rest of Virginia, it has had a unique history of settlement and development influenced by agriculture, fishing, tourism, and the Pennsylvania Railroad.

William G. Thomas describes the Eastern Shore during the late 19th and early 20th century as "a highly complex and interdependent landscape".

As a whole, the Shore is generally a competitive region, but also leans Republican owing to Accomack's larger share of the population.