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The Arcade is an historic building at 31 Circuit Avenue in Oak Bluffs, Massachusetts. Built in the early 1870s, it is one of the best preserved buildings on Circuit Ave, and is further locally significant as housing the offices of the Oak Bluffs Land and Wharf Company, which was responsible for much of the early development of the town of Oak Bluffs. The property was listed on the National Register of Historic Places in 1994.

The Dr. Harrison A. Tucker Cottage is a historic summer cottage at 61 Ocean Avenue in Oak Bluffs, Massachusetts. The cottage took shape in the 1870s as a combination of several smaller structures that were joined by an addition. Doctor Tucker was a resident of Cottage City, as Oak Bluffs was then known, and invited Ulysses S. Grant during his time there. Tucker was also a leading figure in the Oak Bluffs Land and Wharf Company, which spearheaded development of the town outside the Methodist meeting camp known as Wesleyan Grove. The house was listed on the National Register of Historic Places in 1990, for its association with Dr. Tucker, and as one of the most elaborate Victorian houses in the town.

Oak Bluffs is a census-designated place (CDP) in the town of Oak Bluffs, Dukes County, Massachusetts, United States, on the island of Martha's Vineyard. The Oak Bluffs CDP comprises the most densely settled part of the town, including the neighborhoods of Vineyard Highlands, Harthaven, and part of Eastville. Oak Bluffs was first listed as a CDP prior to the 2020 census with a population of 2,324.

Union Chapel (or the Oak Bluffs Christian Union Chapel) is an historic octagon-shaped church building in Oak Bluffs, on Martha's Vineyard, Massachusetts. The church was built in 1870 as a non-sectarian worship space in an area dominated by the Methodist summer camp meeting known as Wesleyan Grove. Acquired in 2002 by the nonprofit Martha's Vineyard Preservation Trust, the building continues to be used for nonsectarian religious services, and also serves as a community center and performing arts space.

Wesleyan Grove is a 34-acre (14 ha) National Historic Landmark District in Oak Bluffs, Massachusetts on the island of Martha's Vineyard. Named after John Wesley, the founder of the Methodist Church. Also known as the Martha's Vineyard Campmeeting Association (MVCMA) or the Campgrounds, it was the first summer religious camp established in the United States. It is famous for its approximately 300 colourful cottages in a style now described as Carpenter Gothic.

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.

Harthaven is a community in the town of Oak Bluffs located on Martha's Vineyard in Dukes County, Massachusetts, United States.

East Chop, also known as the Vineyard Highlands, is a residential area located in the town of Oak Bluffs, Massachusetts on the north end of the island of Martha's Vineyard. It is a peninsula surrounded on the North and East by Vineyard Sound and on the West by Vineyard Haven Harbor, and features the high, prominent bluffs that gave Oak Bluffs its name. A lighthouse, East Chop Light, stands at the north end of the chop on Telegraph Hill. East Chop has no obvious commercial businesses or stores, although it has a private yacht and beach club, the East Chop Beach Club. East Chop became a popular summer resort in the late 19th century. A steamship wharf, known as Highland Landing or Highland Wharf, served regular ferry traffic from the mainland during the 1890s, and a horse railroad connected it to the village of Cottage City, later renamed Oak Bluffs. East Chop and the Highlands became a popular camp meeting gathering ground for Baptists, and church members erected a wooden tabernacle in 1877. The remains can still be seen in Temple Park.

East Chop Light is a historic lighthouse standing on a bluff overlooking Vineyard Haven Harbor and Vineyard Sound, located along East Chop Drive in the town of Oak Bluffs, Massachusetts. It is one of five lighthouses located on the island of Martha's Vineyard.

Martha's Vineyard Hospital is a not-for-profit regional medical center located in Oak Bluffs, Massachusetts. Founded in 1921, it is the only hospital in Dukes County.

Farm Neck Golf Club is a semi-private golf club located in Oak Bluffs, Massachusetts, United States. In the 1970s, a real estate company named Strock Enterprises intended to create a golf course and housing developments on a peninsula within the town but locals felt they were not maintaining a conservationist ethic. The Supreme Judicial Court of Massachusetts ruled against Strock which soon thereafter went bankrupt. Farm Neck Associates then bought the territory and created a golf course with the intent to preserve the environment. The 18-hole course has earned plaudits from notable publications and hosted President Clinton and President Obama while on vacation.

The Ritter House (also the Jirah Luce House) is an historic house on Beach Street in Vineyard Haven, Massachusetts, USA, and is listed on the National Register of Historic Places. The house is one of the few remaining Federal period buildings in Vineyard Haven. It has had a succession of occupants and uses, and as of 2007 served as a retail establishment.