Gwynn's Island is an island located in the Chesapeake Bay on Virginia's Middle Peninsula. The island is located in the northeast part of Mathews County, south of the mouth of the Piankatank River. It is connected to the rest of the county by a swing bridge over Milford Haven. The communities of Gwynn and Grimstead are located on the island.
Archeological evidence found on Gwynn's Island indicates that the island was inhabited as early as ten thousand years ago. In 1642, Hugh Gwynn of Jamestown purchased the island; he and his family became the first English settlers there. Gwynn's Island served as a base for Lord Dunmore, the last royal governor of Virginia, after the burning of Norfolk. A smallpox outbreak and attacks by the revolting patriots led Dunmore to leave the island in the summer of 1776.
- Cronin, William B. (2005). The Disappearing Islands of the Chesapeake. Maryland Historical Society. p. 182.
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