Warrosquyoake Shire

Warrosquoake Shire (with numerous variant spellings, including Warrascoyack, Warrascocke and "Warwick Squeak") was officially formed in 1634 in the Virginia colony, but had already been known as "Warascoyack County" before this. It was renamed Isle of Wight County in 1637.

Shortly after the establishment of Jamestown in 1607, English settlers explored and began settling areas adjacent to Hampton Roads. The shoreline region of Warrascoyack was then occupied by the Warraskoyak tribe of the Powhatan Confederacy, under their weroance, Tackinekintaco. The main Warraskoyak village was located in present-day Smithfield, Virginia, while a satellite village called Mokete was at Pagan Point, and another called Mathomank was on Burwell's Bay under a sub-weroance named Sasenticum. In December 1608, Captain John Smith left Samuel Collier, his page, with Tackinekintaco to learn the language.

The first English plantation in the region, dating to 1618, was that of Puritan merchant Christopher Lawne, and several other Puritans also seated themselves nearby, including Edward Bennett in 1621. He named his plantation Warrosquoake, after the river that also went by the same name. It was heavily hit in the Great Massacre of 1622, losing 53 of the 347 persons killed that day. The plantation was briefly abandoned until a fort could be built nearby; the Warraskoyak Indians were driven off from their villages in the reprisals of the following years. A census of settlers on 16 February 1623 shows a total of "33, including 4 negroes". Another census a year later showed a total population of 31 settlers for the region.

Edward Bennett represented his plantation in the 1628 House of Burgesses, then left for England. The following year, the "County of Warascoyack" was represented by his nephew, Richard Bennett, Captain Nathaniel Basse, and three others, all Puritans. This was the Puritans' strongest representation in the Anglican-dominant colony.

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