Martha’s Vineyard: The Playground of the Rich & Famous

The playground of the rich & famous

by Mary Luz Mejia.

President Obama and his family vacation here, alongside the Clintons, actors Bill Murray and Meg Ryan, and scores of well-heeled authors, journalists, artists and dreamers. “The Vineyard” as the island of Martha’s Vineyard and neighbouring Chappaquiddick Island are called, offers picture-perfect sunny days, miles of windswept beaches and seclusion.


Air or boat-only access makes it a perfect getaway for the rich and famous seeking privacy. It’s a unique destination for those who love seafood, history, and balmy beaches. If that sounds like you, we’ve rounded up some of The Vineyard’s finest sights and sounds for those planning to stay awhile this summer.

Where to Eat and Drink

Island life and dining is a relaxed affair. At the award-winning State Road restaurant in West Tisbury, that means made-from-scratch, modern American cuisine. A popular stop for both locals and visiting presidents, State Road features robust brunches, seafood-heavy dinners with fresh local ingredients and burger night menus. If you’re looking for a more laid-back vibe, Red Cat Kitchen delivers delicious with a side of sass. Savour chef and owner Ben Deforest’s cheeky—and epic—menu items, including a Pan Crisp Skin-On Line Caught Codfish, or Deep Cold Water Lobster and Niman Ranch Pork Belly served with hominy grits. If you don’t have allergies or aversions, take a walk on the “Wild Side” and order his tasting menu.

Where to Shop

Situated in scenic Oak Bluffs, the contemporary American craft gallery Craftworks is a local favourite. Peruse hand-crafted pottery, jewelry, furniture, wood, and metal home accents created by hundreds of artists from The Vineyard and beyond. Next stop should be Alley’s General Store in West Tisbury. Known as the “dealers in almost everything” Alley’s will set you up with everything from beach basics and hostess gifts, to pantry staples like milk and bread. It’s the oldest retail business on The Vineyard—a meeting place and an island tradition kept alive by the folks who call the region home.

Things to See and Do


Bike over to the scenic Aquinnah Cliffs, where the hundred-million-year-old story of this island unfolds in ribbons of multi-coloured sand, gravel and clay. Don’t miss the iconic red-brick Gay Head Lighthouse, open seasonally for tours with the lighthouse keeper. And in pretty Oak Bluffs, be sure to take in over 300 pastel-hued Gingerbread Cottages, complete with delicate, lace-like trimmings and woodwork. The cottages have sweet names to match their appearance, such as “Wooden Valentine” and “Angel Cottage”, pure eye candy!

Where to Stay

Isabelle’s Beach House in Oak Bluffs.

If you’re after a true New England cottage experience, consider staying in a seaside bed and breakfast like Isabelle’s Beach House in Oak Bluffs. The sprawling front porch and many of the house’s rooms offer panoramic ocean views. Each room is outfitted in pretty, casual beach decor and includes private bathrooms. In Chilmark, you can stay at the Menemsha Inn and have the innkeepers take care of your every need—or rent one of their 12 cottages, complete with fireplace (for cooler months), kitchens, bedrooms and seating areas. Best of all is that serene ocean view—every cottage has one—that makes The Vineyard a perfect place to detox, recharge and relax.


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