Gwynn Island Favorite Tips by grandmaR

History of Gwynn's Island

Favorite thing: Gwynn's Island was originally settled by Col. Hugh Gwynn in 1634. The legend goes that the colonel and two of his servants were admiring the island when they saw a sudden squall upset an Indian girl's small dugout canoe. She turned out to be the daughter of the chief of the Piankatank tribe. In gratitude for her rescue, he was given the island. He also obtained an official grant from the English proprietor.

Some maps and charts (and VT) have the name as Gwynn Island, but island historians insist that it should be Gwynn'S Island, just like Martha's Vineyard.

Fondest memory: During the Revolutionary War, after Lord Dunsmore the Royal Governor burned Norfolk, he assembled a fleet of more than 180 ships loaded with loyal Tories and they took over Gwynn's Island, looting and devouring all the livestock. From here they raided other settlements, notably the eastern shore islands such as Tilghman, James and Sharps. Eventually the local militia drove off Dunsmore's group and mounted a cannon at Cricket Hill on the mainland. Some think that it was the cannon and some think it was the fever which killed more than 500 of the Tories which drove Dunsmore and company off the island. The Coast Guard station now occupies the site of the cannon.

Additional information at Gwynn's Island Museum history page