The Gwynn’s Island Historic District encompasses approximately 1,425 acres at the northern tip of Mathews County. The Gwynn’s Island Historic District maintains ties to its 380-year heritage of farming and maritime trade anchored by the Chesapeake Bay. In the present day, much of the architecture on the island strongly reflects the “summer cottage” or resort community that developed starting in the 1920s. Surviving historic structures and landscapes on the island continue to face dangers associated with global warming and climate change, such as rising waters and storm surges. Gwynn’s Island was originally occupied by Virginia Indians starting in the Paleoindian period, approximately 10,000 to 15,000 years ago. Europeans first settled on the island following Hugh Gwynn’s 1642 patent. The population grew over the next two centuries and the island’s period of historical significance begins in 1776 after the establishment of earthworks at Fort Cricket Hill and the Battle of Gwynn’s Island during the American Revolutionary War. The history of Gwynn’s Island is inextricably tied to the Africans and African Americans who helped build the island’s economy, community, and culture beginning as early as the 17th century. While the contributions of Africans and African Americans are difficult to discern in the island’s current cultural landscape, their stories are remembered by Virginians elsewhere throughout the state: from an origin story linked to Black indentured servants, to one of the first-known cases of enslavement of an African individual in Virginia, to the formation of a Revolutionary War-era British “Ethiopian” regiment of escaped enslaved men and their tragic fate, to the Black watermen and oystermen who built their lives on the island after the Civil War only to be forced off their property during the Jim Crow era. The island’s historical significance concludes in 1972, after the establishment of The Islander Hotel representing the peak of the district’s transition into a recreational destination.