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Isle of Wight's history takes root in 1619 when English settlers, already having an established colony at Jamestown, crossed over to the south side of the James River to begin a new settlement. This settlement was named Isle of Wight Plantation in 1621 after the known English home of one of the settlers, Sir Richard Worsley, and probably those with him. During the years that followed, ships traveled back and forth to Isle of Wight, England and the surrounding areas to obtain supplies and more settlers.

Isle of Wight County's history continued to grow. In 1634, Isle of Wight, originally known as Warrosquoyacke (an Indian name meaning Point of Land), was formed as one of the eight original shires (or counties) into which Virginia was divided by the General Assembly of the Colony of Virginia.