Martha’s Vineyard is more than a picturesque coastal escape—it’s a cornerstone of African American history, culture, and legacy. For over a century, the island has served as a rare and powerful symbol of Black prosperity, community, and cultural preservation, making its history both unique and deeply significant.
Oak Bluffs: One of America’s First Black Vacation Communities
The story begins in Oak Bluffs, one of the only places in the early 1900s where Black families could freely vacation and purchase property. During segregation, when most resorts and beaches were off-limits, Oak Bluffs became a safe and welcoming destination. African American middle-class families began building cottages—many of which still stand today—creating one of the first longstanding Black vacation communities in the United States.
The Shearer Cottage: A Historic Safe Haven
A key landmark in this history is the Shearer Cottage, opened in 1912 as one of the first inns in Oak Bluffs to welcome Black guests. It hosted some of the most prominent figures of the 20th century, including Madame C.J. Walker, Paul Robeson, and W.E.B. Du Bois. At a time when discrimination limited travel options, places like the Shearer Cottage provided dignity, comfort, and a sense of belonging.
A Hub for Black Excellence and Leadership
Over the decades, Martha’s Vineyard evolved into a seasonal gathering place for Black leaders, creatives, and professionals. Notable visitors and homeowners have included President Barack Obama, Spike Lee, Oprah Winfrey, and Vernon Jordan. These figures didn’t just vacation here—they contributed to a culture of excellence, networking, and influence that helped shape national conversations around race, politics, and art.
The Inkwell Beach: A Symbol of Resilience
Another powerful site is Inkwell Beach, historically one of the few beaches where Black visitors were allowed. While the name has complex origins, the beach has been reclaimed as a symbol of pride and resilience. Today, it remains a central gathering place, rich with cultural meaning and community tradition.
Why This History Still Matters
The importance of Martha’s Vineyard Black history lies in its role as both refuge and representation. It tells a story of how Black Americans created spaces of joy, ownership, and cultural identity despite systemic barriers. Today, preserving this history helps ensure future generations understand not only the struggles—but also the triumphs—that shaped this iconic destination.
Stay at Surfside Hotel
Nestled in the heart of Oak Bluffs, our dog-friendly hotel is one of the premier lodgings in the area. Choose from accommodations with ocean-view rooms, garden views, modern amenities, and enough space for the entire family. We are a short four-minute walk from Ocean Park and a convenient location for exploring the rest of the island!
Our seaside accommodations are proud to be family-owned and operated since 1987. We look forward to welcoming you and your family to your home away from home at Martha’s Vineyard Surfside Hotel. Book your vacation with us today!