Whether you’re looking for a quick weekend getaway to Massachusetts’ most famous island — or a longer stretch of time with a longer stretch of beach — there are a few great ways to spend your “summah” vacation, as the locals say.
Each adventure to Martha’s Vineyard begins with a trip on the Steamship Authority ferry and if you think you want to have a car to adventure around here from busier Oak Bluffs to chilled-out Chilmark (and its completely worth-a-drive chocolate shop), get your tickets early. Most folks who have come here for years wind their watch by when the coveted vehicle transportation tickets go on sale. But fear not — it’s pretty easy to get around on foot, by bicycle, shuttle or even car rental.
It’s even easier when you stay in the heart of the action and, after a quick 45-minute ferry from the mainland over, you’re stepping foot on the Obamas’ favorite vacation spot. Take a walk back in time when you head to Summercamp to check in, a whimsical resort reimagined by Boston interior design mastermind Rachel Reider, whose preference for blue hues are just perfect for the oceanside locale. Retro-chic interiors — including beds hung by rope swings, and bow-and-arrow and firefly décor — all pay homage to the property’s former life as a seasonal retreat, and the game room and its massive table tennis thunk-thunk back and forth at the entrance set the soundtrack for a fun weekend.
There’s a great view of the harbor from the wraparound porch to watch the passersby, or take a walk to the Gingerbread Cottages just a couple of blocks away for a Candy Land-like stroll to admire the colorfully painted turn-of-the-century wooden homes. If it’s sweets you’re after, there are plenty here, including Mad Martha’s ice cream shop downtown (if you spill any, there’s also more than a few t-shirt shops to get some new vacation duds). Those with younger kids may want to hold off on the snacks until after a spin on the nation’s oldest platform carousel, Flying Horses. Try to gather the brass ring on the colorfully painted steeds and you can win a free ride.
Take a spin of another kind on a rental bicycle over to where the bridge where Jaws was filmed along Seaview Avenue. Jumping off is not encouraged, but dips in the water are easier anyway at the two-mile stretch of sand with shallow water where the movie was filmed: Joseph Sylvia State Beach. If a combo of names like Barack, Malia and Sasha float your boat, then the Red Cat Kitchen is where dinner should be in order, as the former President preferred the seafood here — and the island is chock-full of good options. You won’t go hungry at Biscuit, either, around the corner from Summercamp; try the eponymous indulgence or savory breakfast potatoes in their jackets. Donut-lovers can grab their breakfast at Martha’s Vineyard Gourmet Café and Bakery, or try a little bit of luck at night at the Café’s Back Door Donuts — the line strings around the block here on hot nights for a fresh-basked treat.
Those with a bit more time — and a taste for lazing — will enjoy a week at Winnetu resort on the other side of the island in Edgartown. This pristine complex of three- to five-bedroom private home rentals, one- to four-bedroom hotel suites and rooms is on one of the sleepiest parts of the 87-mile island, albeit with one of the best stretches of sand at South Beach. With two outdoor heated pools, a tasty restaurant, fitness center and Oceanside yoga classes, a tennis club and kids programming — including an antique fire truck that makes the rounds every afternoon for kids to climb on, a gigantic chess board and turtle pond — you may consider not even leaving. (There is a free shuttle to the white-picket-fence downtown, however.)
If you have a car, the friendly international concierge staff will recommend a circuitous route or rent you one for to be conveniently delivered to the front door of the resort. Even better — the island’s circuitous route makes it difficult to get lost since there’s basically just one road. Grab a pastry at Morning Glory Farm before heading to Long Point Wildlife Refuge, where the story trail leads to great ocean views and the chance to spot colorful birds. Alley’s General Store is like taking a walk back in time, too, with its penny candy, snacks and sand-friendly souvenirs, all within a trek to the outdoor Field Gallery and its free-for-all sculptures. Check out Chilmark Chocolates next, or grab a heartier lunch at Larsen’s Fish Market for what most locals call the best lobster roll on the island. Whether you choose one drizzled in warm butter or smothered in creamy mayo, one thing is certain — you’ll need plenty of napkins to be able to grip your rental’s steering wheel en route to the island’s most iconic site: Gay Head Lighthouse and Cliffs.
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