Martha's Vineyard Has Been America's Quietest Old-Money Address for a Century

Martha's Vineyard, the island off Cape Cod in Massachusetts, has been a fixture of American old-money summering since well before it became shorthand for it. The Kennedy family has kept compounds on and around the island for decades, and its beaches, weathered-shingle houses and lack of chain development have long made it a low-key counterpart to the more visibly showy resort towns further down the East Coast.

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A presidential habit

Bill Clinton vacationed on the island through much of his presidency, and Barack and Michelle Obama have returned regularly since his time in office, buying a waterfront property near Edgartown's Great Pond in 2020. The purchase, reported at the time at roughly $11.75 million for a nearly 30-acre compound, cemented a pattern of sitting and former presidents treating the island as a discreet, press-tolerant retreat rather than a place to be seen.

Old money without the ostentation

What distinguishes Martha's Vineyard from other historic East Coast enclaves is a long-standing local preference for low profiles: grand houses tend to sit behind hedges and unpaved driveways rather than gates and stone walls, and the island's small towns, Edgartown, Vineyard Haven and Oak Bluffs among them, still function as working communities rather than seasonal stage sets. Jackie Kennedy Onassis kept a home on the island for years, and a number of prominent figures in entertainment and media, including Spike Lee, have owned property there for decades.

Getting there is part of the filter

The island has no bridge; access is by ferry from Cape Cod or by a limited number of small-plane and seasonal charter routes, and car reservations on the main ferry route fill up well ahead of summer weekends. That logistical friction, more than any formal exclusivity, has long done a lot of the work of keeping the Vineyard's crowds thinner than its reputation might suggest.

Traveller tips

• The Steamship Authority ferry from Woods Hole is the main vehicle-carrying route to the island; car reservations should be made well in advance for summer travel.
• Edgartown, Oak Bluffs and Vineyard Haven each have a distinct character; Edgartown is the most historic and formal of the three.
• Late summer and early autumn bring quieter beaches and lower rates than the peak July-August season.
• Much of the island's most sought-after real estate is privately held and not visible from public roads; respect posted private property.