Template:Wp-Isle of Wight County, Virginia-History

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During the 17th century, shortly after establishment of the settlement at Jamestown in 1607, English settlers explored and began settling the areas adjacent to the large Hampton Roads waterway. Captain John Smith in 1608 crossed the James River and obtained fourteen bushels of corn from the Native American inhabitants, the Warrosquyoack or Warraskoyak. They were a tribe of the Powhatan Confederacy, who had three towns in the area of modern Smithfield. English colonists drove the Warraskoyak from their villages in 1622 and 1627, as part of their reprisals for the Great Massacre of 1622, in which the Native Americans had decimated English settlements, hoping to drive them out of their territory.

The first English plantations along the south shore within present-day Isle of Wight were established by Puritan colonists, beginning with that of Christopher Lawne in May 1618, and Edward Bennett (colonist) in 1621. Several members of the Puritan Bennett family also settled there, including Edward's nephew, Richard Bennett. He led the Puritans to neighboring Nansemond in 1635, and later was appointed as governor of the Virginia Colony.

By 1634, the entire Colony consisted of eight shires or counties with a total population of approximately 5,000 inhabitants. Warrosquyoake Shire was renamed in 1637 as Isle of Wight County, after the island off the south coast of England. The original name had come derived from the Native Americans of the area; it went through transliteration and Anglicisation, eventually becoming known as "Warwicke Squeake".

On October 20, 1673, the "Grand Assembly" at Jamestown authorized both Isle of Wight County and Lower Norfolk County to construct a fort.

St. Luke's Church, built in the 17th century, is Virginia's oldest church building. In the late 20th century, it was designated as a National Historic Landmark in recognition of its significance. Many landmark and contributing structures on the National Register are located in Smithfield including the Wentworth-Grinnan House.

In 1732 a considerable portion of the northwestern part of the original shire was added to Brunswick County, and in 1748 the entire county of Southampton was carved out of it.

During the American Civil War, Company F of the 61st Virginia Infantry Regiment of the Confederate Army was called the "Isle of Wight Avengers."