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.
By 1634, by order of the King of England, Charles I, eight shires of Virginia were formed with a total population of 4,914 settlers. Warrosquoake Shire included 522 persons at this time. It and Accomac Shire were the only shires given Native American names for the friendly tribes nearby. It was renamed Isle of Wight County in 1637, after the Isle of Wight, an island in the English channel. The river bearing this name was renamed Pagan River.
During the three years when it was officially Warrosquoake Shire, Richard Bennett led the small Puritan community to neighboring Nansemond, and later fled with them to Maryland. He returned during the Cromwellian period to serve as Governor of Virginia.
Land that was originally portions of the Warrosquoake Shire and Isle of Wight County later formed many other counties to the immediate southwest, in the region now defined as Southside Virginia. Isle of Wight County, Southampton County, Greensville County and Brunswick County were all created within the limits of what had been Warrosquoake Shire.