Famous for its hundreds of colorful, picturesque gingerbread cottages in a lovingly preserved historic community, Oak Bluffs on the Massachusetts island of Martha’s Vineyard is a quintessential New England resort beach town. So successful as a 19th-century Methodist summer retreat, Oak Bluffs inspired an underrated Rhode Island beach destination. Seven miles off the mainland, Martha’s Vineyard perfectly captures the charm of rural English villages. The island is no stranger to historic preservation, which results in beautifully maintained towns full of character like posh Edgartown with its cobblestone streets and gray-shingled homes and businesses. Add lighthouses, beaches, windswept dunes, marinas packed with boats, and just-caught seafood, and it’s no wonder that Martha’s Vineyard is a popular summer destination for all. Generations of Black Americans created a community in Oak Bluffs including luminaries like Adam Clayton Powell Jr., Henry Louis Gates, Jr., and Vernon Jordan. Former U.S. President Barack Obama and his family have also been regular visitors.
Being an island, Martha’s Vineyard is not that hard to get to. You can fly to the island from cities like New York and Washington, D.C., or take a ferry from the mainland town of Falmouth on Cape Cod to Edgartown. Make your travel arrangements as far ahead as possible in summer as flights, ferries, and inns get booked months in advance. Martha’s Vineyard Airport in West Tisbury is seven miles from Oak Bluffs and approximately the same distance from Edgartown.
Oak Bluffs’ architectural significance and beaches
In 1866, landscape architect Robert Morris Copeland was commissioned to design Cottage City (renamed Oak Bluffs in 1907), an early-American planned residential community that emphasized pedestrian-friendly layouts with winding paths and communal green spaces. Although well laid out, the community is best known for its Carpenter Gothic cottages, often referred to as “gingerbread houses.” These structures are characterized by their ornate trim, vibrant colors, and intricate woodwork. A National Historic Landmark, Oak Bluffs is overseen by the Martha’s Vineyard Camp Meeting Association (MVCMA). There are more than 300 cottages here plus the Tabernacle — a large, open-air pavilion used for community events. In its heyday, 20,000 people attended service here. Explore on your own or join a regularly scheduled MVCMA walking tour in the peak season months of July and August.
Oak Bluffs has several beaches, all open to the public. The two-mile Joseph Sylvia State Beach borders Oak Bluffs and Edgartown, and Eastville Beach is near Vineyard Haven. Oak Bluffs Town Beach is the most convenient, as it’s right by the ferry terminal, harbor, and downtown with its restaurants and shops. A section of the town beach called Inkwell Beach has long been a popular recreational spot for African Americans. There are 41 sites on Martha’s Vineyard’s African American Heritage Trail – you can follow a map or learn about the island’s deep ties to the Black community on a Martha’s Vineyard African American Heritage Trail tour.
What to do and where to stay in Oak Bluffs
