Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. The population was 5,341 at the 2020 United States Census. It is one of the island's principal points of arrival for summer tourists, and is noted for its "gingerbread cottages" and other well-preserved mid- to late-nineteenth-century buildings. The town has been a historically important center of African American culture since the eighteenth century.

Martha's Vineyard, often simply called the Vineyard, is an island in the U.S. state of Massachusetts, lying just south of Cape Cod. It is known for being a popular, affluent summer colony, and includes the smaller peninsula Chappaquiddick Island. It is the 58th largest island in the U.S., with a land area of about 96 square miles (250 km2), and the third-largest on the East Coast, after Long Island and Mount Desert Island. Martha's Vineyard constitutes the bulk of Dukes County, Massachusetts, which also includes the Elizabeth Islands and the island of Nomans Land.