Oak Bluffs is a town located on the northeast shore of Martha's Vineyard in Massachusetts, United States. It serves as one of the island's principal points of arrival for summer tourists, functioning as a terminal for ferry boats arriving from the mainland. The town sits on the northeast shore, bordered by Nantucket Sound to the north and east, Edgartown to the south, and Vineyard Haven Harbor, Lagoon Pond, and Tisbury to the west. Its harbor is a key maritime hub, connecting the island community with various mainland destinations through multiple ferry services.

The area was originally inhabited by the Wampanoag people for approximately 10,000 years and was known as Ogkeshkuppe, meaning damp or wet thicket. Europeans settled the region in 1642, where it remained part of Edgartown until 1880. It was officially incorporated as Cottage City that year before re-incorporating in 1907 as Oak Bluffs, named for an oak grove along bluffs overlooking Nantucket Sound. The town was consciously planned by developers who established the Oak Bluffs Land and Wharf Company, making it the only Martha's Vineyard town developed specifically with tourism in mind.

The community is noted for its unique gingerbread cottages and well-preserved mid-to-late-nineteenth-century Carpenter's Gothic architecture. These structures, originally built for Methodist camp meetings at Wesleyan Grove, feature elaborate wooden scrollwork and bright paint schemes. The Tabernacle, a circular open-sided pavilion, and the Flying Horses Carousel, the oldest platform carousel still in operation, are significant landmarks. The Campground grounds and buildings were declared a National Historic Landmark in 2005, recognizing their historic value.

Oak Bluffs has been a historically important center of African American culture since the 18th century, welcoming black tourists when other island towns did not. Affluent African Americans from New York, Boston, and Washington bought homes in areas like the Oval, transforming the town into a premier vacation spot by the 1930s. The Inkwell beach became a famous gathering place for this community. The town also hosts the Martha's Vineyard Summer Institute, established in 1878 as the first summer school for teachers in the United States.

The population was 5,341 at the 2020 United States census. The town covers a total area of 26.0 square miles, with 71.61 percent being water. Access is primarily via five ferry operators connecting to Woods Hole, Falmouth, Hyannis, New Bedford, and Quonset Point. The compact layout allows visitors to walk off the ferry and explore the town or its four public beaches on foot. The economy relies heavily on seasonal tourism, supported by the island's accessibility and historic attractions.