New England sea captains’ houses framed with white picket fences. Flying horses alongside ice cream shops. Colorful gingerbread cottages on one end of the island and an authentic fishing village on the other. Lighthouses pierce the fog with their signals. A Native American community preserves its identity amid miles of pristine beaches and rolling farmland. Martha’s Vineyard is a picturesque island indeed.

If you can imagine Martha’s Vineyard as the shape of a humpbacked whale, up on the “hump” you’ll find two of the island’s main towns, bustling Vineyard Haven and resort-y Oak Bluffs. The coast slopes from there down to the “head,” Edgartown, with its more dignified (some would say snooty) New England charm. The “underbelly” is a long stretch of ocean beach, deeply indented with ponds and inlets, leading to the glorious Aquinnah cliffs, the western “tail” of the island. The Vineyard’s western half—“up island” as the locals say—is hilly and rural, with a few tiny but delightful hamlets.

Things to Do

Bicycle the shaded paths that hug the coastline. Stroll down to lively Circuit Avenue in Oak Bluffs for a Mad Martha's ice cream cone and then ride the Flying Horses Carousel, the oldest working platform carousel in the country. Cheerful Victorian gingerbread cottages enliven its bustling harbor. Wander past the manicured lawns of regal 18th-century homes in gentile Edgartown before taking a short ferry ride to visit the peaceful preserves of Chappaquiddick Island. Or just soak up the sun at Aquinnah Beach, against a backdrop of dazzling red clay cliffs.


Stop by the Edgartown Scrimshaw Gallery for a hand-carved ivory memento of the sea. Afterward, walk Main Street for island wear, souvenirs and trinkets. Head down-island on the country roads to West Tisbury, where you can buy bread at the Scottish Bakehouse, and Chilmark for a stop at Allen Farm to buy sweaters made from the wool of their flock of over 200 sheep.

Nightlife and Entertainment

All towns except Oak Bluffs and Edgartown are dry, and the last call at bars and clubs is midnight. In Oak Bluffs, Circuit Avenue is the center of the rowdiest bar and live music scene and the best nighttime street life. In Edgartown, you may have to hop around a few wine bars and low-key pubs before you find the evening's most happening spot.

Restaurants and Dining

Restaurants tend to be expensive on the Vineyard, but the stiff competition has produced a bevy of places that offer excellent service, evocative settings and creative cuisine. Try fresh lobster or bay scallops on Main Street or smoked salmon in a Victorian house in Oak Bluffs. It wouldn't be New England without a lobster roll, especially those in the fishing village of Menemsha. When you want a break from seafood, stop for a juicy burger at the humble harbor shack Black Dog Tavern in Vineyard Haven -- a true Vineyard experience.