Artists, celebrities and presidents flock to Martha’s Vineyard for the quintessential New England getaway. Located seven miles off the southern coast of Cape Cod, the Vineyard is less developed than the Cape and more cosmopolitan than neighboring island Nantucket: Picture an abundance of farms and fisheries set against windswept pastoral and ocean vistas. Springtime is when the island really comes back to life, with flowers in bloom and shops and restaurants reopening for the season. At just 100 square miles, the Vineyard is split between down-island and up-island towns—and it’s an easy drive and ferry ride from Massachusetts, New York or Rhode Island.
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Daniel EddyChef at New York’s Rebelle, whose family has had a home in Martha’s Vineyard since the 1930s
“Martha’s Vineyard is a bit of a time capsule. There still are many things that operate as they may have many years ago that you don’t see off-island: People hitchhike, people barter, farm stands operate on honor system, and people still use landlines.”
This all-day dining spot is legendary for its epic sandwiches and top-notch bakery. Order the jalapeno cheddar biscuit with sausage, egg and cheese.
Larsen’s Fish Market
Local oysters and clams (and other shellfish) are in demand at this take-out spot. Pro tip: Call ahead and place your order earlier in the day, then eat your catch on the dock or the beach at sunset.
The Black Dog Tavern
The waterfront standby is steps from the main ferry. Its interior is decorated with boat tackle and other nautical touches, but try to grab a picnic table outside if you can.
The Sweet Life Cafe
Chef Carlos Montoya, formerly of New York’s Aureole, serves French-leaning classics like steak tartare in a romantic Victorian townhouse. It’s one of the Obamas’ favorite spots on the island.
Many of the ingredients at this modern American joint are sourced from the restaurant’s own garden. Drop by for Burger Night every Thursday for five different variations, like lamb or spicy chickpea.
The Red Cat Kitchen
There isn’t a bad seat in the house at this vibrant, bold take on market fare. Inside, you’re surrounded by art by locals and live music; outside you’re under the flattering glow of paper lanterns.
West Tisbury Farmers Market
Nearly 40 vendors sell produce to farmers, locals and visitors every Wednesday and Saturday.
Alley’s General Store
Built in 1858, it’s the oldest operating store on Martha’s Vineyard. Grab your morning coffee and picnic supplies here before hitting the beach.
Eileen Blake’s Pies and Otherwise
The original Eileen’s daughters carry on their mother’s flaky, double-crusted pie-baking tradition. The strawberry-rhubarb, pecan and Toll House pies are all standouts.
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The Outermost Inn
Perched on Gay Head Cliffs, this seven-room inn is surrounded by the sea and untouched landscapes.
Winnetu Oceanside Resort
The 54-suite resort has all the amenities you’d expect (gym, library), plus surprising ones like a putting green and a turtle pond. It’s a mere 250-foot walk to the beach.
Once a 19th-century Gothic revival home, the Hob Knob is now the island’s chicest ecofriendly boutique hotel, complete with a farm-to-table breakfast and afternoon tea.
Long Point Wildlife Refuge
West Tisbury’s nature reserve encompasses 600 acres of dunes, easy hiking trails and protected coastline.
More than 300 brightly painted “gingerbread cottages” with ornate wooden trimmings can be found in this colony. Check out the especially Instagram-worthy Pink House.
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