Cuttyhunk Island is the outermost of the Elizabeth Islands in Massachusetts. A small outpost for the harvesting of sassafras was occupied for a few weeks in 1602, arguably making it the first English settlement in New England. Cuttyhunk is located between Buzzards Bay to the north and Vineyard Sound to the south. Penikese Island and Nashawena Island are located to the north and east respectively.

The Elizabeth Islands are a chain of over 20 small islands extending southwest from the southern coast of Cape Cod, Massachusetts in the United States.They are located at the outer edge of Buzzards Bay, north of Martha's Vineyard, from which they are separated by Vineyard Sound, and constitute the town of Gosnold in Dukes County, Massachusetts.