Martha’s Vineyard has always been a unique island and vacation destination, made even more diverse with the arrival of Black homeowners in the nineteenth century. 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, Joneses 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.