Located just south of Cape Cod, the triangular-shaped island of Martha’s Vineyard is undeniably one of the most exclusive summer hideaways in the U.S. For such a jet-set destination, however, it also maintains a reputation for friendliness. (Case in point: Strangers tend to wave at each other on the expansive beaches, something not often seen in such upscale enclaves.)
These unique elements make the Vineyard an especially perfect destination for a summer such as this one. Good vibes and spacious outdoor landscapes abound, and the island boasts a soothing charm. It feels a world away from the crowded bustle of the Northeast’s metropolitan cities.
Just short of 100 square miles and encompassing a handful of welcoming towns, the Vineyard offers a variety of vastly different “scenes”. There’s the peerless allure of Edgartown, from the quietude of the farmland to the gingerbread cottages. There’s also the remote, otherworldly coastal beauty of its western villages (chief among them is Aquinnah, aka Gay Head). Adding to its idyllic ambiance, iconic New England lighthouses dot many a spit of sand.
This peaceful summer paradise is easily accessible by Tradewind Aviation’s scheduled or private service flights. For those looking for a much-needed escape, here’s how to spend a weekend in Martha’s Vineyard. Each of the establishments we’ve highlighted is ready to safely welcome guest. This ensures your getaway is relaxing and stress-free — as any Vineyard weekend in Martha’s Vineyard should be.
4 p.m. Check into Harbor View Hotel, which celebrates its 130th anniversary this year and recently underwent a top-down renovation of its coastal-contemporary décor. Harbor View is a mere three-minute bike ride away from Edgartown, located less than half a mile. This hotel is the quintessential Vineyard abode. Amenities include an outdoor, heated seawater pool, as well as a new fitness center. At the hotel, the main inn is the center of the action. However, families should take note of the specialty accommodations. These include the one- to three-bedroom Captain’s Cottages and the 2,270-square-foot Presidential Skyhouse (boasting four beds, five baths, and spectacular views).
6:30 p.m. An Edgartown institution courtesy of Eli Levy and Jamie Zambrana, the Atlantic Fish & Chophouse is beloved for its USDA Prime steaks, whole branzino, and numerous lobster dishes, from the lobster arugula salad to the lobster ravioli with beurre blanc — and especially the crowd-pleasing black truffle lobster mac & cheese. Don’t leave without trying the decadent five-layer Valrhona chocolate cake or the French-style Nutella cheesecake. If you’re opting for take-out, enjoy it at nearby Lighthouse Beach at dusk.
9 a.m. Massachusetts is blueberry country, so rise and shine and head down to Bettini, the Harbor View’s all-day restaurant, for blueberry buttermilk pancakes. After breakfast, stroll into town along North Water Street to admire the waterside homes festooned with globes of blue hydrangeas. It takes just 10 minutes to hit the town center, where you can browse contemporary art at Eisenhauer Gallery, casual wear at the iconic Black Dog, and women’s apparel and jewelry at Nell. Don’t miss the excellent indie bookstore, Edgartown Books, and be sure to grab some chocolate pecan fudge for later at Murdick’s, which has been using the same recipes since 1887.
12 p.m. Pick out a beach cruiser at Martha’s Vineyard Bike Rentals, then if you’re up for an easy, hour-long bike ride, hop on and pedal to South Beach. The Vineyard is known for its well-paved bike paths, and the ride is flat and rural. After seeing the narrow strands of sand around Edgartown, you’ll find South Beach to be a shock. Accessible over grassy dunes, the Hamptons-like beach is long and wide, with golden sands.
5 p.m. Cool off with a refreshing dip at the hotel pool, and order up a cocktail from the Roxy pool bar. (We recommend the refreshing One in a Melon, made with vodka, watermelon, and basil.) For dinner, walk over to the casual Seafood Shanty: The local oysters from Katama Bay, the tuna roll, and the lobster quesadilla are standouts.
10 a.m. Explore more of the island by car (hint: you can borrow a Mercedes from the hotel, one of its many stylish amenities). One of the more unusual spots is the Oak Bluffs Campgrounds, where hundreds of Victorian-era cottages show off their candy colors. Then head out to far-flung parts west, to Chilmark and the clay cliffs of Aquinnah, and keep your eyes peeled for the Chilmark General Store, where you can load up on a picnic brunch of kale salads, baguette sandwiches, fresh-baked banana bread, and cinnamon rolls.
Finally, drive to Tisbury at the northern tip of the Vineyard to admire the West Chop Lighthouse, which dates from 1891 and stands 45 feet tall. It’s a wonderfully fitting way to cap off a visit to one of the Northeast’s most classic communities.
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