When the English arrived in Chesapeake Bay, the native Americans supposedly referred to the Eastern Shore as Accawmacke - the "across the water place" or "land beyond the water."1 Assuming that is an accurate description of the meaning of the word, the English were talking with Native Americans who recognized the Eastern Shore was isolated by the Chesapeake Bay.
Spelling of Accomack has varied over the years. The General Assembly finally resolved in 1940 that the county name would be spelled with a "k," as Accomack County, but the town that serves as the county seat is still spelled Accomac without the "k." There is just one other place in the United States called Accomac, and no other place spelled with the "k" in the name.2
English settlement of "Ye Plantation at Accawmacke" came early. The natives on the Eastern Shore were friendly, and access to the area by boaat was relatively easy compared to walking into the interior past the Fall Line. The Chesapeake was a highway, rather than a barrier, in the 1600's.
In 1634, Accomack was created as one of the first 8 local jurisdictions (initially called shires rather than counties) in the colony of Virginia, decentralizing government services from Jamestown. The original Accomack County covered the entire Eastern Shore; today's Accomack County is just half of its original size. The original Accomack County covered the entire Eastern Shore; today's Accomack County is just half of its original size.
In 1643, the local jurisdiction's name was changed to Northampton County, perhaps because the leading citizen on the Eastern Shore (Obedience Robins) sought to honor his home territory in England - and perhaps as part of an effort to select English rather than "heathen" aboriginal names. Robins was been a supporter of Lord Cromwell and the Parliamentarians who controlled England - and finally Jamestown - in the 1650's.
By 1663, both Obedience Robins and Lord Cromwell were dead, King Charles II had been restored to the English throne, and the Royalists were back in charge in Jamestown. The General Asembly divided the Eastern Shore into two counties, and the northern half of the peninsula next to Maryland was given the original name of Accomack County. Obedience Robins' rival, the Royalist Edmund Scarborough (or Scarburgh), ensured that the southern boundary of Accomack County was drawn more than halfway down the peninsula towards Cape Charles. The boundary left 50% of the Eastern Shore population in Northampton County, but significantly more than half the acreage on the Eastern Shore was placed in Scarborough's Accomack County. Scarborough also worked with Maryland officials to define the northern boundary of Accomack County, and managed to get the boundary line drawn north of the actual 38th parallel.

Scarborough's influence in Jamestown did not last. By 1670, Governor William Berkeley wanted to arrest Edmund Scarborough for threatening the Native Americans and Quakers on the peninsula, even those in Maryland. Scarborough's reported murder of several Native American chiefs was one of many Anglo/Algonquian incidents that ultimately culminated in Bacon's Rebellion, a civil war within the colony of Virginia in 1676.
However, Scarborough claimed to be the burgess for Accomack, and therefore immune from arrest. The protection from arrest prevented the King (or his governor in the colony of Virginia) from harassing the legislators when there were major disagreements. Without immunity, the King/governor could arrest elected representatives to block them from voting in the House of Burgesses.
Governor Berkeley eliminated Scarborough's immunity by abolishing Accomack County in 1670. This eliminated Scarborough's position as a representative from Accomack county, and thus his protection from arrest. Scarborough died in 1671, eliminating the conflict - and the next General Assembly re-created Accomack county. In 1687, the General Assembly responded to complaints from Northampton County and adjusted the boundary northward, to the current line between Occohannock Creek and Matchapungo Creek.3
