Why Martha's Vineyard Has Been America's Discreet Summer Address for Generations

Martha's Vineyard, an island a few miles off the southern coast of Cape Cod, Massachusetts, has spent more than a century as one of the United States' most consistently low-key summer addresses. It has no traffic lights anywhere on the island, six small towns rather than one built-up centre, and a long list of prominent seasonal residents who have mostly been left alone by design rather than accident.

An island split into six small towns

The island is divided into six towns: Edgartown, Oak Bluffs, Vineyard Haven, West Tisbury, Chilmark, and Aquinnah, each with a distinct character. Edgartown's white clapboard sea captains' houses and harbourfront reflect its 19th-century whaling wealth, while Oak Bluffs is known for its Victorian "gingerbread cottages", rows of brightly painted, ornately trimmed houses built originally as a Methodist camp meeting ground in the 1860s.

A well-documented presidential habit

Bill and Hillary Clinton began vacationing on the island in the 1990s and have returned regularly since, and Barack and Michelle Obama spent multiple summers there before buying a home near Edgartown in 2019. The island's appeal to a low-profile crowd tends to be less about any single figure and more about the number of people who have quietly built the same summer habit over decades.

Beyond the harbour towns

Up-island, the towns of Chilmark and Aquinnah are far less developed, home to the Aquinnah Cliffs, a National Natural Landmark of striped red and white clay rising above the Atlantic at the island's western tip, and Menemsha, a working fishing harbour that still sells the day's catch straight off the boats.

Traveller tips

• Cars are best left off the ferry in peak summer; the island's town centres are walkable and connect by a seasonal shuttle bus.
• Ferries from Woods Hole on Cape Cod run year-round; summer sailings for cars sell out weeks ahead.
• The Flying Horses Carousel in Oak Bluffs, running since 1876, is one of the oldest continuously operating carousels in the country.
• Book accommodation months ahead for July and August, when the island's population multiplies several times over.