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Less crowded than the Hamptons, but more accessible than neighboring Nantucket. Martha’s Vineyard has long been the summer getaway of choice for presidents—the Obamas, Clintons and Kennedys have all holidayed there—and well-heeled New Englanders looking to kick back and relax. An island-wide “no chain store” rule has kept Martha’s Vineyard blissfully disconnected from the mainland. There are no traffic lights or parking meters on the island – or vineyards (G+Ts are the beverage of choice). Here is our guide to the perfect weekend on The Vineyard.

Where to Stay

The Hob Knob

The Hob Knob Hotel, is a classic 19th-century Gothic Revival. Built on Upper Main Street in Edgartown whose guests have included President Kennedy. After a day exploring the island’s beaches—the hotel provides guests with beach cruiser bikes, gourmet picnic lunches, beach chairs, and umbrellas. You can also enjoy a frosty pitcher of homemade lemonade on the wraparound porch. In Edgartown there are three new, boutique style hotels owned by Lark Hotel group: The Christopher, The Sydney, and the Richard. All offer more contemporary, brightly decorated rooms with in-room iPads, Apple TV, and free Wifi as well as complimentary beach bags and chairs.

Sitting on a picturesque bluff above Vineyard Haven harbor, the Nobnocket Inn is a 1908 Arts & Crafts-style house. The house has been converted into a seven room boutique hotel. Showcasing modern designers and artists featuring pieces by Marcel Wanders, Moooi, Caligaris, Knoll, Philippe Starck, Robert Held, Sarah Holl, Bill Evaul and more. The aesthetic is elegant but minimalist with parquet floors, natural light, and views to die for.

Where to Eat and Drink

Opened in 1943, the Artcliff Diner in Vineyard Haven is the breakfast and brunch spot that has visitors and locals lining up for pancakes, eggs, bacon and homefries on the daily. Bring a book. You will have to wait for a table. If you are in Edgartown, head to Behind the Bookstore for pour-over coffee and warm rice pudding with black plum and preserved lemon. You can work up an appetite cycling to the Right Fork Diner. There you can watch the biplanes take off and land at the historic Katama grass airfield over lobster eggs Benedict.

Beach picnic lunch provisions can found at The Black Sheep right off of Main Street in Edgartown. If you’re heading Up Island stop at 7a Foods for a roasted beet wrap or a Liz Lemon sandwich with housemade pastrami, turkey, swiss, coleslaw, Russian dressing on rye. Book ahead if you want to dine the Obamas favorite restaurant, The Red Cat Kitchen in Oak Bluffs. Or get a seat at the Black Dog Tavern clam chowder. Hot new dinner spots in Edgartown include The Covington for farm-to-table plates and fresh pasta, and Raw 19 Oyster Bar for “shucking amazing” oysters, smoked blue fish, and lobster. 

What to Do

Summer is all about creating the perfect balance of surf and turf. Get an oversand vehicle (OSV) permit and take the Chappy Ferry for a 527-feet journey across the Edgartown Harbor to Norton Point Beach for a day of swimming and fishing. Preorder a picnic or get a full clambake delivered. The clambak comes complete with lobster trap tables, torches, and an enclosed fire pit from The Kitchen Porch

Alternatively, paddleboard around Menemsha Pond. A picturesque salt pond split between the towns of Aquinnah and Chilmark and home to the island’s indigenous Wampanoag tribe. The tribe who have inhabited the shores of the pond for approximately 10,000 to 7,500 years. Afterwards head over to Menemsha Beach to catch the sunset while feasting on fresh locally caught lobster and clams and farmstand corn.

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