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Every family has somebody who knows the stories behind the stories. They remember whose ambition began the family’s legacy, who owned the house where everyone gathered, and who made a way when there wasn’t one. On Martha’s Vineyard, the African American Heritage Trail has spent nearly three decades making sure the island’s Black history is remembered with that same care.

Martha’s Vineyard’s reputation as a beloved summer destination for Black families is well earned. Its history also includes the people who established businesses, created gathering places, built institutions, and challenged discrimination so that future generations could live, work, rest, and return. Much of that history remains visible throughout the island, from the cottages of Oak Bluffs to the waterfront of Edgartown, where ordinary-looking places hold extraordinary stories about Black life.

The African American Heritage Trail of Martha’s Vineyard exists to preserve and share those stories. Through historical research, educational programming, guided tours, and commemorative markers, the nonprofit has spent nearly three decades documenting the lives and contributions of people of African descent on the Massachusetts island. What began as an effort to address the absence of local Black history in schools has developed into an expansive preservation initiative, with more than 40 recognized sites across Martha’s Vineyard.

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The Heritage Trail originated through the work of Elaine Cawley Weintraub and Carrie Camillo Tankard, two women who met in 1989 and discovered a shared commitment to making the island’s Black history accessible to residents, particularly students. Weintraub, an educator and historian, had become concerned about the absence of local African American history from classroom materials. Her research eventually led her to birth certificates, burial records, wills, and other archival documents that revealed generations of Black life largely missing from the island’s public historical narrative.

Tankard, who served as vice president of the Martha’s Vineyard branch of the NAACP, had already spent years advocating for more inclusive historical education. Her efforts included distributing educational materials to local schools and organizing exhibits about African American history in the island’s libraries. Together, the two women developed a plan to install permanent markers at historically significant locations, giving residents and visitors an opportunity to learn about the people and events connected to the places they encountered in everyday life.

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Their original vision involved just four sites. In 1998, the Heritage Trail dedicated its first landmark, Shearer Cottage, a historic Black-owned guesthouse in Oak Bluffs that welcomed African American vacationers during an era when racial discrimination limited their lodging options. Established by Charles and Henrietta Shearer, the cottage became an important gathering place for Black travelers, including prominent intellectuals, artists, and professionals. Its recognition helped establish a framework for documenting the island’s broader African American history through the physical places where that history unfolded.

The project eventually expanded beyond Oak Bluffs, recognizing people and places connected to the island’s maritime industries, religious institutions, education, civil rights activism, and cultural life. Today, the Trail’s documented landmarks illustrate a history that stretches back centuries, encompassing experiences of enslavement, emancipation, migration, entrepreneurship, and community-building.

In Chilmark, for example, the Trail recognizes Rebecca Amos, an African woman who was enslaved on Martha’s Vineyard during the 18th century. Her family history connects generations of enslavement and emancipation to the life of her great-grandson, William A. Martin, a Black sea captain whose homestead and gravesite are also recognized by the Trail. At Edgartown Harbor, another marker commemorates Esther, an enslaved Indigenous woman who escaped captivity in 1743. While being transported from Boston to North Carolina, Esther reportedly escaped from a ship anchored in the harbor despite extraordinary efforts to restrain her. The location was subsequently recognized by the National Park Service’s Underground Railroad Network to Freedom.

Other landmarks commemorate abolitionist Frederick Douglass, Harlem Renaissance author Dorothy West, pioneering Black politicians, educators, entrepreneurs, and community organizations. Among them is Cottagers’ Corner in Oak Bluffs, which honors The Cottagers, an organization of African American women established in 1956. Through community service, educational initiatives, and cultural programming, its members helped strengthen the island’s social fabric while establishing traditions that have continued across generations.

While some Heritage Trail landmarks recognize nationally prominent figures, others commemorate people whose names may be unfamiliar to visitors but whose contributions were essential to everyday life on the island. Business owners, tradespeople, hospitality workers, and families who opened their homes to travelers helped sustain Martha’s Vineyard’s growing Black community. Their stories have become an important part of the organization’s efforts to document the island’s economic and cultural history.

In 2021, the Heritage Trail received a $120,000 grant through the National Trust for Historic Preservation’s African American Cultural Heritage Action Fund. The investment supported additional research, staffing, community outreach, and storytelling focused on historically Black-owned businesses. Fallon Samuels Aidoo, a Tulane University preservation professor and consultant who has worked with the African American Heritage Trail of Martha’s Vineyard, helped advance this work, which expanded the organization’s ability to identify and document enterprises that had served generations of island residents and visitors.

According to Aidoo, the grant supported the recognition of three sites in particular: Dunmere by the Sea, Taylor’s Playfair, and Graves Shop & House. Each represents an important part of the island’s Black entrepreneurial history and the businesses that supported community life.

Dunmere by the Sea, for example, is a historic Oak Bluffs cottage that served African American visitors during the Jim Crow era. Under the ownership of Joseph A. and Calvin B. McBride, the property offered Black vacationers accommodations and access to the beach. It was listed in the 1964 edition of the Negro Motorist Green Book, a travel guide that helped Black Americans identify welcoming establishments during segregation. The cottage’s history illustrates how hospitality businesses provided opportunities for Black travelers while creating economic possibilities for the people who operated them.

In 2023, the Trail also recognized Robert and Shirley Graves, whose Graves Machine and Tool Company operated in Oak Bluffs. The dedication marked the first site in a Black Business Trail initiative documenting historic and contemporary entrepreneurship. By recognizing businesses like the Graves family’s enterprise alongside guesthouses and other hospitality establishments, the organization is also expanding the public’s understanding of the industries in which Black islanders worked and built their livelihoods.

The expanded research has also created opportunities to examine the relationship between historic Black businesses and those operating on Martha’s Vineyard today. “One of those individuals, Jeffrey Burnett, developed a digital interface combining historical businesses in the Green Books with contemporary entrepreneurship recorded in India Rose’s Black Business Directory,” Aidoo said. Established in 2019, Rose’s Martha’s Vineyard Black-Owned Business Directory helps make local Black-owned enterprises more visible and accessible to residents and visitors. Aidoo said the comparison provides insight into how the island’s entrepreneurial landscape has evolved, noting, “The overlaps in industry and geography are remarkable but I find more fascinating what’s different.”

The research offers another way of understanding how earlier generations of Black entrepreneurs helped establish an economic foundation for those who followed. It also places contemporary Black business ownership within a longer historical context, connecting establishments that served Black travelers during segregation with the entrepreneurs serving residents and visitors today.

The Heritage Trail has continued adding sites as new histories are documented. In June 2025, it dedicated its 41st landmark, the Dragonfly House in Oak Bluffs. The historic property once provided lodging for Black visitors and had connections to John Ritchie, an abolitionist who documented the experiences of the 54th Massachusetts Infantry Regiment during the Civil War. Its recognition illustrated how a single property could preserve multiple chapters of American history, from abolitionist organizing to Black hospitality and contemporary community-building.

The Heritage Trail supports historical education, youth mentorship, scholarships, and employment opportunities. Its research also helps identify places deserving additional protection and recognition, particularly as properties change ownership and older generations of residents pass on. For visitors interested in exploring the island through its history, the organization offers guided cultural heritage tours and resources for learning about its recognized sites.

The importance of this work extends beyond identifying historical landmarks. Houses change hands, businesses close or evolve, and neighborhoods can look entirely different from one generation to the next. Without documentation, the people who contributed to those places can gradually disappear from public memory, even as the buildings and streets associated with their lives remain.