How Black Businesses Built A Legacy On Martha’s Vineyard — And What It Takes To Preserve It

On Martha’s Vineyard, a spare bedroom could be both a business strategy and an act of hospitality. For generations, Black homeowners have turned their properties into places where visitors could stay, families could reunite, and entrepreneurs could earn a living. These arrangements helped make summers on the island accessible to more Black Americans while establishing economic opportunities for the people who called it home.

The history of Black homeownership on Martha’s Vineyard is as much about what people did with their properties as it is about who owned them. Across generations, families purchased modest cottages, established businesses, offered accommodations, and created networks that allowed others to experience the island. Their efforts contributed to the development of the cultural destination that Black Americans continue to enjoy today.

Among them were Charles and Henrietta Shearer, whose Oak Bluffs property became one of the island’s best-known Black-owned hospitality establishments. Henrietta operated a successful laundry business before the couple opened Shearer Cottage as an inn in 1912, providing accommodations for African American travelers during a period when racial discrimination restricted their lodging options. The property became a gathering place for Black visitors, including prominent artists, intellectuals, and professionals. Today, the family’s history remains an enduring example of how property ownership and entrepreneurship helped sustain the island’s Black community.

The Shearers’ story is familiar to those acquainted with the island’s history, but their experiences also reflect a much broader tradition of Black families using the resources available to them to build businesses, support their neighbors, and establish a presence that could endure for generations.

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