It is named after the Isle of Wight, England, south of the Solent, from where many of its early colonists had come.

[4] Isle of Wight County is in the Virginia Beach-Norfolk-Newport News, VA-NC Metropolitan Statistical Area.

Isle of Wight County features two incorporated towns, Smithfield and Windsor.

In 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.

By 1634, the entire Colony consisted of eight shires or counties with a total population of about 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 Anglicization, eventually becoming known as "Warwicke Squeake".

Many landmark and contributing structures on the National Register are in Smithfield including the Wentworth-Grinnan House.

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