The first people of African descent to live and work on the island were slaves or servants. By the early 19th century, slavery was gradually abolished in northern states and most of the people of color were servants. Over time, the African Americans on the island began owning property and living on the island year-round. Some of these families also became small business owners and entrepreneurs. The existence of a small black enclave provided options for renting rooms and summer homes, and this brought more African American visitors to the island from a variety of Eastern cities. Many of the property and businesses owned by African Americans in the late 19th and early 20th centuries continue to be owned and operated by their descendants.
After World War II, more African Americans moved to Oak Bluffs on Martha’s Vineyard and brought their families for permanent residence. They bought houses which have dramatically increased in value over the years and Oak Bluffs continues to be an important community for many African Americans as an example of self-determination as well as a model for integration as diverse families live and vacation in the area.