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.

The New England cottages of Martha’s Vineyard have been a summer getaway for the African-American elite for more than 100 years. Drawn to the harbors of Oak Bluffs in the late 1800s, freed slaves and laborers began settling there.

In 1866 Robert Morris Copeland was hired by a group of New England developers to design a planned residential community in Martha's Vineyard. The site, a large, rolling, treeless pasture overlooking Vineyard Sound, was adjacent to the immensely popular Methodist camp meeting, Wesleyan Grove, a curving network of narrow streets lined with quaint "Carpenter's Gothic" cottages, picket fences, and pocket parks. Seeking to take advantage of the camp’s seasonal popularity (and overflowing population), the developers established Oak Bluffs Land and Wharf Company, gaining immediate success: Five hundred lots were sold between 1868 and 1871. Copeland would end up creating three plans for the community to accommodate its constant expansion. Oak Bluffs is the one of the earliest planned residential communities and largely informed later suburban development in the United States.

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