Weekend Retreat: Martha's Vineyard

Where to Eat

So you just arrived on the island and you’re famished. Skip the ferry hot dog and chowder, and stop in at Jimmy Sea’s. Hidden behind Oak Bluffs’ bustling Circuit Avenue is the perfect spot to enjoy a sensational meal upon arrival, or enjoy that last hurrah before returning to the mainland. This tiny Italian restaurant with a family atmosphere serves up creamy, flavorful dishes.

Next, step into some Vineyard Vines threads (the island’s official uniform), and go to the place to be seen: Atria’s in Edgartown, where islanders and vacationers alike enjoy the sophisticated food in the main dining room. Or, simply relax in the chic downstairs bar.

After a long night of sipping cocktails (this is a vacation after all) you’ll need some serious morning sustenance–and perhaps a Bloody Mary or two. The Art Cliff Diner in Vineyard Haven is at your service with frittatas, green eggs and ham, and other breakfast staples you’ll surely be craving. But if you’re in the mood for something sweeter, try a “Belly Bomb” at Humphrey’s Bakery. The name of the icing-filled doughnut doesn’t hide any surprises. But, trust us, it’s worth it.

Where to Stay

To work off some of those vacation libations, you might want to stay at the Winnetu Oceanside Resort, where you won’t want to spend a minute inside. The hotel’s amenities include tennis courts, yoga, and fitness classes. There’s also a putting green, outdoor ping pong, and life-size chess, as well as access to South Beach and a heated pool. If privacy is more your thing, check into the hotel’s fully equipped cottage that includes a kitchen, living room, and sprawling ocean side deck.

Want to make like the Kennedy’s and stay in a compound? You can live the life at the Beach Plum Inn. Located in Menemsha, the inn includes 11 luxury rooms and cottages, tennis and croquet courts, a private beach, and a restaurant. Guests would never leave the grounds if not for Aquinnah’s stunning cliffs, mud baths and private beaches.

Taking a trip with the whole family? There’s a plethora of family activities at the Harbor View Hotel & Resort, located in the heart of Edgartown. A recent 77-million-dollar overhaul has added brand new kitchens and revamped cottages to fit all your little ones, and the Harbor Kids Club allows children to explore the island with chaperones, so mom and dad can kick back and relax. Be sure to also visit Boucle Salon & Spa.


Anyone who’s anyone goes to the fair (including Jake and Maggie Gyllenhaal, Reese Witherspoon and kids, and Meg Ryan). The Martha’s Vineyard Agricultural Fair starts Aug. 21 and runs through the weekend. From backwoods country music to fried treats, farm animals, and giant zucchini, the fair is all about old-fashioned country fun. Enjoy the good-spirited competitions, including the woodsmen contest, skillet tossing, and a dog show.

Pick up a new beach chair and Maui Jims at Island Pursuit and spend an afternoon on Chappy, Martha’s Vineyard’s quintessential beach hangout that inspired Judy Blume’s best seller Summer Sisters. Bask in the sun on the beaches of Wasque (pronounced way-squee) where visitors can explore rare grasslands or drive their cars onto the beach for an afternoon picnic. No car? Pedestrians can hop the Chappaquiddick Ferry and walk a short two miles to the beach.

Artists have flocked to the Vineyard for years, making the Granary Gallery at the Red Barn the perfect place to scour for original artwork. This quaint country gallery houses art exclusively created by island artists. Local artists also display their crafts at the Vineyard Artisans Summer Fair at Grange Hall, home of the West Tisbury Farmers Market. The market is a meeting ground for locals, artists, and farmers selling everything from fresh produce and artisan bread, as well as Alpaca sweaters, paintings, and botanicals. Now there’s where you’ll find a Vineyard souvenir worth taking home.