Just in time for your summer Friday: our Music Editor’s definitive guide to the legendary vacation destination of American political and celebrity royalty—and your next weekend getaway.
By Haley Albert
A staple of the Chilmark community. “The Store,” as it’s often referred to, is everybody’s first stop in the morning. Grab a blended coffee or frozen lemonade, or a “Road Race” sandwich (chicken and avocado on ciabatta—a personal favorite) and eat it on the porch in one of the Store’s adorable, nostalgic rocking chairs.
7 State Rd, Chilmark, MA 02535
While Chilmark has nailed quaint, rural and romantic, those looking for a shopping district (or the Martha’s Vineyard equivalent) should head to Edgartown. During the day it’s the perfect place to rent bikes from Anderson’s Rentals and cruise beachside.
For eats, you’ll find the best food at Alchemy, or the Port Hunter (one of the newer restaurants to hit Main Street) and you absolutely must hit Mad Martha’s for ice cream afterwards. Be sure to pick up a tee from The Black Dog shop— if only so everyone knows where you were over the weekend.
8 Union St, Vineyard Haven, MA 02568
5 Water St, Vineyard Haven, MA 02568
This is where all your wicker-chair, flowers-in-rattan-baskets, farm-to-table dreams come true. The Beach Plum is one of the most picturesque places to stay on the Menemsha/Chilmark border. Whether in the main house or in a luxe-yet-quaint nearby cottage, you are within seconds from Menemsha Fish Market and Lucy Vincent Beach, a private beach for guests—like yourself—only.
Although the sleeping accommodations are a Restoration Hardware-phile’s dream, it is the restaurant in the Main House that makes this place so perfect. Lauded by the New York Times as one of the best restaurants on the island, The Beach Plum celebrates the Vineyard’s tight-knit community of farmers and fisherman with delicious food on a rotating menu of about ten to twelve items.
53 Circuit Ave, Oak Bluffs, MA 02557
LUCY VINCENT BEACH
The exclusive beach with the golden gates (or, rather, wooden security shed) is a gratis perk with your stay at the Beach Plum, Once you get onto the beach, hang a left and take a stroll past the dividing cliff, and you will have stepped onto the island’s nude beach. Europe meets New England. Those without Beach Plum reservations can always hide in the back of someone’s car that has a drive-on pass (a foolproof trick from an expert beach crasher!)
Lucy Vincent Beach Rd, Chilmark, MA 02535
You’ll likely end up stocking (and restocking) up on Chilmark Chocolates before vacation’s end. These are fresh and sumptuous gourmet chocolates that make the perfect gift for friends at home, and also your stomach (treat yourself). My recommendation: the Dark Chocolate Caramel Bark.
19 State Rd, Chilmark, MA 02535
If you want a Lobster Roll, you go to Larsen’s. Period. End of description.
56 Basin Rd, Chilmark, MA 02535
Boasting some of the most beautiful views on the island, The Cliffs look almost like a dreamy, picturesque pastel drawing. The location is densely populated with tourists, and for good reason. The Aquinnah Shop Restaurant overlooks the Cliffs and is great for breakfast or lunch, but don’t come too hungry—waiting an hour for a table is usually the standard.
27 Aquinnah Cir, Aquinnah, MA 02535
ICE HOUSE POND
Trying to put this place into words is difficult. Some Vineyard residents call it magical (yes, really), and boast of its healing powers, while some prefer it as a late night skinny-dipping spot. But one thing is agreed upon: this eleven-acre freshwater pond, surrounded by scrub oak and a tall grove of pitch pines is bliss. Hidden in the woods off of Lamberts Cove road, this secret pond is the the most peaceful place to swim on the island—if you can manage to find it. Since the pond is an ecosystem for some of the most rare and endangered creatures on the island, there are a limited amount of people allowed in the pond at once. If you do nothing else while you’re in Martha’s Vineyard, you must convince a local to help you navigate the woods and find this little bit of heaven.