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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“Black homeowners on the island have always created communities of economic importance to the island.” Fallon Samuels Aidoo, a Tulane University preservation professor and consultant, told MadameNoire. Her work examines the relationships among property ownership, entrepreneurship, migration, and the development of Black communities on the island, revealing an economic history that extends beyond its reputation as a summer retreat.

Following the American Revolution and the abolition of slavery in Massachusetts, Afro-Indigenous islanders worked alongside Black immigrants and migrants, establishing networks that connected Martha’s Vineyard to communities throughout the Caribbean, Canada, and other parts of the Black Atlantic. According to Aidoo, these networks helped recruit and manage skilled labor for island industries, including hospitality, maritime infrastructure, lumber, and brickmaking. Their contributions helped establish an economic foundation for the island while creating employment opportunities for Black workers and their families. The importance of Black labor to the island’s early development is also reflected in the history of African Americans working in New England’s maritime and whaling industries.

The growth of Black communities on Martha’s Vineyard, however, did not necessarily correspond with widespread property ownership. Although the island eventually attracted successful Black professionals and families with considerable financial means, much of its earlier Black population consisted of working people whose opportunities for homeownership were limited. Aidoo described the distinction between visiting the island and owning property there in her own words: “Modest is how I’d describe Black homeownership then and now. The socioeconomic mobility that Black folk achieved after the Civil War, Great Migration and immigration materialized in many more Black folk on the Vineyard but mostly as renters.”

For homeowners, renting out a room or a cottage could provide an additional source of income while expanding access to the island for other Black families. Aidoo described how these arrangements contributed to the island’s tourism economy: “Our rental income in summer has been an economic driver of island tourism since the early 1900s, when people of color dwelled in “camp” structures and rented out a room in someone’s cottage.” These arrangements supported a growing network of accommodations, allowing visitors without the means to purchase property to establish their own relationships with the Vineyard.

One example of this tradition was Aunt Georgia’s House, a guesthouse operated by Georgia O’Brien and Louisa Izett at 121 Lower Circuit Avenue in Oak Bluffs. According to the African American Heritage Trail, the women provided room and board to Black travelers for $7 a week during an era when racial restrictions shaped where people of color could purchase property and find accommodations. Their establishment was among the businesses that helped make the island accessible to African Americans who might otherwise have struggled to secure lodging.

As the Civil Rights Movement helped open additional economic opportunities, more Black Americans were able to purchase properties and establish permanent or seasonal residences on the island. According to Aidoo, the growth in Black property ownership during this period expanded opportunities for other people of color to visit Martha’s Vineyard, find employment, enjoy leisure, and reconnect with their communities.

The relationship between homeowners and renters became an important part of the island’s social and economic development. Property owners could generate income, while visitors gained access to accommodations and experiences that might otherwise have been financially or socially inaccessible. Over time, these connections helped sustain the traditions that continue to bring generations of Black families to Martha’s Vineyard each summer.

While the Shearer family is frequently celebrated for its contributions to the island’s hospitality industry, Aidoo emphasizes that Black entrepreneurship on Martha’s Vineyard developed through the collective efforts of numerous families whose histories deserve greater recognition.

She identifies the Shearer and Coleman families as examples of households that combined business ownership, employment, and cultural expression with community-building. Their contributions extended beyond individual properties or establishments, helping create an environment where Black cultural traditions became integral to the island’s social life.

Aidoo explained why their histories deserve recognition: “The story of the Shearer and Coleman families are often told and much celebrated—rightfully so. They’re instructive of how Black families of little means have made the island a place for others, not just themselves, to enjoy. The heads of these households—women and men—operated businesses on island and off, carried more than one job, recruited and invited likeminded people to join them, employed peers and youth, and made cultural practices such as the building and performing arts part of their placemaking.” Their example demonstrates how entrepreneurship helped create opportunities that extended beyond individual households, making it possible for more people to participate in the island’s growing Black community.

The Coleman family’s legacy is documented at Coleman Corners, an African American Heritage Trail site in Oak Bluffs. Luella Barnett Coleman first arrived on Martha’s Vineyard in 1927 to work as a summer waitress. In 1944, she and her husband, Ralf Meshack Coleman, purchased a property that became a gathering place for their children and grandchildren. Ralf, a celebrated actor, playwright, producer, and director, also contributed significantly to Black theater in Boston, bringing another dimension of artistic and cultural achievement to the family’s legacy.

Aidoo also points to other families whose contributions helped shape the island’s history but have received comparatively less public attention. Aidoo explained, “Others such as the Pollards of Virginia and Taylors of Providence (and the Caribbean) and the Goughs of Nova Scotia and Correiras of Cape Verde were equally successful and influential during the same period of Black homebuilding and wealth building—and they spoke out about colorism and classism while doing so.” Their experiences reflect the diversity of the island’s Black population, including families who arrived through migration, employment, and entrepreneurial opportunities, as well as those who challenged inequalities within their own communities.

The island’s history is also inseparable from its Indigenous residents, whose relationships with the land extend far beyond the establishment of Martha’s Vineyard as a vacation destination. Aidoo emphasized, “Let’s not forget Native islanders—Wampanoag and Chappaquiddick tribe members of color—never left this place or stopped placemaking.” Both the Wampanoag Tribe of Gay Head (Aquinnah) and the Chappaquiddick Wampanoag Tribe document their longstanding connections to the island, including histories of land stewardship, cultural preservation, and resistance to displacement.

Together, these histories demonstrate how Black homeownership and entrepreneurship developed through relationships among people of different backgrounds, economic circumstances, and generations. While some families established businesses that catered to seasonal visitors, others operated enterprises that met the needs of people living and working on the island throughout the year.

The African American Heritage Trail’s Cottage Business Project has documented properties and enterprises that provided lodging, dining, laundry, childcare, home repairs, and other essential services. The research illustrates how Black-owned cottages and small businesses functioned as important economic and cultural institutions, supporting both the tourism industry and everyday community life.

Aidoo explained, “Historically, Black businesses provided the spectrum of services and goods that a person of color would need to live on the island long term.” Although the island’s year-round Black population has grown considerably since the 1960s, she said the range of Black-owned businesses serving permanent residents has only recently begun to reflect that growth. Builders, designers, and decorators are increasingly joining established Black real estate brokers and property managers in industries that support homeownership and property maintenance.

Contemporary entrepreneurs continue expanding that economic landscape. In 2019, resident India Rose established the Martha’s Vineyard Black-Owned Business Directory, creating a resource that helps residents and visitors identify and patronize local Black-owned enterprises. Businesses represented in the island’s contemporary entrepreneurial community span industries including hospitality, beauty, retail, food services, and real estate. The directory has since expanded from a digital resource into a printed guide, extending the visibility of Black-owned businesses to visitors planning their trips and residents interested in supporting the local economy.

Their presence continues a tradition in which Black economic participation has helped sustain the community’s cultural identity. The businesses that serve seasonal visitors remain an important part of that economy, but so do the professional and service providers whose work supports everyday life on the island. Together, they represent the ongoing relationship between economic opportunity and the ability to establish and maintain a place within the community.

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The properties that helped generations of Black families establish themselves on Martha’s Vineyard now exist within one of Massachusetts’ most challenging housing markets. According to a Massachusetts state housing assessment, approximately 61% of the island’s homes are designated for seasonal or occasional use, based on 2018-2022 census estimates. High property values, limited year-round housing availability, and the demand for vacation properties have created significant affordability challenges for residents. These challenges have also been documented by the Martha’s Vineyard Commission, which studies the island’s housing needs and develops recommendations for addressing its limited supply of year-round housing.

For families who have maintained properties across generations, these pressures can complicate decisions about ownership and inheritance. A home that once represented an attainable investment may now carry substantial maintenance expenses and property taxes, leaving some owners to consider whether they can afford to retain it. The financial considerations can be particularly difficult when a property also holds decades of family history or represents one of the few remaining physical connections to earlier generations.

Aidoo says the surge in real estate investment during the COVID-19 pandemic intensified these challenges for some of the island’s longtime Black homeowners, particularly community elders and their families. As Aidoo recalled, “The exponential rise in island real estate investment during the pandemic put these homeowners and their families in bind—pay the skyrocketing taxes or sell.” Although selling a property may provide immediate financial relief, it can also end a family’s longstanding relationship with a place that has served as a home, gathering space, or source of income for generations.

The economic pressures facing homeowners also raise questions about the future of historically significant properties. While preservation initiatives have helped recognize Black-owned businesses, cottages, and other cultural landmarks, Aidoo believes greater attention must be paid to the resources available to the families responsible for maintaining them. She explained, “The focus on black business at the height of the pandemic was important; I’m proud of our work. But, the island’s Black community also needed similar attention and resources devoted to the modest homes of community elders. There were alternatives that required more preservation and conservation expertise than was made available to them.”

Aidoo observed, “There’s not strong preservation advocacy within the island’s Black community in spite of the abundance of Black heritage, history, and historic property.” She believes preservation must become a more accessible and sustainable practice, particularly for families whose properties are culturally significant but whose financial circumstances may make continued ownership difficult.

Historic recognition can help preserve the stories attached to a property, but it does not necessarily address the financial realities of keeping that property in the family. The Martha’s Vineyard Commission’s historic preservation resources outline the island’s existing historic districts, preservation policies, and protections for culturally significant properties. For homeowners, preservation may also require access to legal guidance, estate planning, conservation resources, and financial strategies that support long-term ownership. These considerations become increasingly important as properties pass between generations and families navigate the competing demands of maintaining their legacies and meeting their present financial needs.

Aidoo sees opportunities to strengthen the relationship between cultural preservation and economic sustainability, making historic properties part of the island’s future rather than simply reminders of its past. She added, “I’m working on that now but it’s going to take a village to make Black heritage preservation a recognizable cultural practice and sustainable business practice.”

The stakes extend beyond individual homes and businesses. Martha’s Vineyard has become meaningful to generations of Black Americans through the relationships, traditions, and shared experiences that connect people to the island. For some, those connections begin with a family property passed down through generations. For others, they begin with a rented room, a familiar business, or an invitation to spend the summer with friends and relatives.