Early landowners included the formerly enslaved Charles Shearer, who along with his wife Henrietta, founded Shearer Cottage. However, the fall of the first Black community on the island came in the 1890s when forty Black and Indigenous people were required to remove their cottages from the Martha's Vineyard Camp Meeting Association. Despite this painful blow, other families, including the Wests, Jones and Huberts bought island homes, challenging restrictive and racist covenants that encumbered the properties. They then passed their homes on to subsequent generations, leading to a legacy of Black homeownership that thrives to this day.

Authors Thomas Dresser and Richard Taylor explore the challenges, triumphs and the sense of community that has endured.