Martha's Vineyard Back to New England

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Courtesy Martha's Vineyard Chamber of Commerce

Despite an A-list patronage—the Obamas are frequent visitors—Martha’s Vineyard is one of New England’s loveliest, and most low key, islands. There are, of course, sophisticated restaurants, shops and hotels (and prices to match), as well as a handful of exclusive private beaches, but at its heart, the Vineyard is about the simple pleasures of summer.

Cheat Sheet

Lay of the Land

Martha’s Vineyard has two distinct faces: Down and Up Island. To non-sailors, the distinction can be confusing at first: Down Island describes the towns in the north and east, while Up Island is the area in the south and west. Those with sea legs, however, understand that traveling west means “going up” in longitude.

Down Island: Down Island is made up of three towns that are the most populated and have many of the island’s best restaurants and shops. Ferries from Woods Hole service Vineyard Haven year-round, on the north shore of the island, which has a picturesque Main Street. East of Vineyard Haven lies Oak Bluffs, which served as one of the country’s most important Methodist meeting places in the mid-1800s. Today it’s known for its beautifully preserved Carpenter-style Gothic gingerbread houses as well as the nation’s oldest elevated carousel, a heavily-touristed but kid-friendly attraction. Edgartown, the most glamorous of the three, is situated in the southeast. First settled in 1642, it became a thriving whaling community that reached its height in the mid-19th century. Streets are still lined with white sea captain’s houses as well as manicured lawns and cute (but overpriced) boutiques. The Chappaquiddick ferry departs from Edgartown’s harbor.

Up Island: Driving west toward Aquinnah, past a backdrop of Technicolor-blue ocean and green rolling hills, dotted with farms and crumbling stone walls, the landscape transforms into something resembling the Irish countryside. Rural Up Island—with its quaint towns of West Tisbury, Chilmark, Menemsha and Aquinnah (formerly Gay Head)—is strikingly different from Down Island.

Up Island is where nature lovers will find the best hiking trails and a fantastic nature preserve, the Polly Hill Arboretum. Art lovers will discover the outdoor sculpture garden at the Field Gallery, and sun worshippers will try to come up with creative ways of gaining access to the gorgeous restricted beaches.

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