Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. The population was 4,527 at the 2010 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 first inhabitants of Oak Bluffs were the Wampanoag people, who have lived on Martha's Vineyard (Wampanoag name: Noepe) for approximately 10,000 years. The area that is now Oak Bluffs was called "Ogkeshkuppe," which means "damp/wet thicket or woods."

The area was later settled by Europeans in 1642 and was part of Edgartown until 1880, when it was officially incorporated as Cottage City. The town re-incorporated in 1907 as Oak Bluffs, named because the town was the site of an oak grove along the bluffs overlooking Nantucket Sound. Oak Bluffs was the only one of the six towns on the island to be consciously planned, and the only one developed specifically with tourism in mind.

People of African descent first arrived at Martha’s Vineyard in the 1600s as enslaved West Africans who worked on the farms of European settlers. The Oak Bluffs harbor drew freed slaves, laborers and sailors in the 18th century, and white locals sold them land. After slavery was abolished, the freed blacks came to work in the fishing industries, in turn drawing black residents from the Massachusetts mainland, who came and started businesses to serve the Vineyard’s growing population. In the 1800s some black laborers also worked as servants to wealthy white families and in the hotels. In the late 19th and 20th centuries, middle-class blacks bought or rented summer homes, and many of their descendants returned annually. Formerly enslaved people, or their descendants, bought property around Baptist Temple Park in the early 20th century, drawn by the religious services held there. Teachers, politicians, lawyers, doctors, artists, musicians and entrepreneurs resided there for decades afterward.

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