Lay of the Land
At just 100 square miles, the Vineyard is split between down-island and up-island towns.
Edgartown: Stately homes of 18th-century whaling captains line the streets of this historic town.
Oak Bluffs: Known for its Victorian cottages and kitschy fudge shops, this is the island’s tourist hub.
Vineyard Haven: Come here for one-off boutiques and the main ferry terminal.
Aquinnah: Make the trek to this western town for its colorful clay cliffs and Gay Head Lighthouse.
Chilmark: Islanders escape the summer crowds for the quiet fishing villages along Chilmark’s coastline.
West Tisbury: The most bucolic area has acres of rolling farmland.
Catch a ferry from Massachusetts, New York, or Rhode Island. If you don’t bring your car, rent a bicycle or a moped. Taxis are also plentiful.
The island has no shortage of charming seaside inns. Here, five that top our list.
Beach Plum Inn: There’s a lot to love about this seven-acre hilltop retreat overlooking Menemsha Harbor, from its clutch of country cottages, where interiors are artful studies in pastels, to the restaurant’s panoramic water views and alpaca pen. Bonus: free passes to the private Lucy Vincent and Squibnocket beaches. Chilmark. $
Charlotte Inn: Towering linden trees frame the clapboard façade of this 1864 merchant’s house. The lobby is full of 19th-century oil paintings and Edwardian objets d’art; upstairs you’ll find 19 intimate rooms done up with plush canopy beds, grandfather clocks, and vintage steamer trunks. $$$
Dockside Inn: At this seaside Victorian Revival, a stone’s throw from the Oak Bluffs ferry terminal, wide wraparound porches are ideal for watching boats sail in and out of the harbor. The backyard garage is stocked with beach necessities, from ice chests to sand toys and loungers, and a 1956 Rolls-Royce is on hand for a spin around the island. Oak Bluffs. $
Hob Knob: Playful elements—dog-shaped lamps; chintz wallpaper—make the Hob Knob ideal for travelers seeking a whimsical alternative to the island’s old-school inns. Take a fishing trip around Vineyard Sound on the hotel’s 27-foot Boston Whaler—and bring back your catch for dinner. Edgartown. $$$
Winnetu Oceanside Resort The 54-suite Winnetu is as close as the Vineyard gets to a mega-resort, with a library, fitness center, and vast lawn outfitted with a nine-hole putting green and a turtle pond. The hotel is just a 250-yard walk from South Beach. $$
Hotel Pricing Key
$ Less than $200
$$ $200 to $350
$$$ $350 to $500
$$$$ $500 to $1,000
$$$$$ More than $1,000
Martha’s Vineyard is all about farm-fresh ingredients and, of course, plenty of seafood.
Black Dog Tavern: A visit to the Vineyard isn’t complete without a stop at this waterfront landmark, mere steps from the main ferry. The rough-hewn interior is decorated with boat tackle and other seafaring objects, but grab a seat at an outdoor picnic table—if one is free. What to order? A lump crab cake sandwich and a bowl of quahog chowder. Vineyard Haven. $$
Hooked: Opened last year, the sibling to popular island spot Atria quickly became the place for in-the-know locals. Its buck-a-shuck oyster happy hour (in July and August) is a perfect prelude to dinner. Look for seafood classics (grilled salmon; soft-shell crab) and offbeat items such as Asian-style baby back ribs. Oak Bluffs. $$
State Road: Many of the ingredients here are picked from the restaurant’s own gardens. Dig into lemon-ricotta pancakes or the locavore burger, with house-made garlic dill pickles, in a wood-beam dining room outfitted with American antiques. West Tisbury. $$$
Sweet Life Café: An alum of New York City’s Aureole, chef Carlos Montoya turns out Frenchified American classics at this romantic Victorian town house—a favorite of the Obamas. Start with a bottle of Chardonnay from the cellar (it’s one of the island’s largest), then try the grilled rib eye with Parmesan velouté followed by a strawberry terrine. $$$
Faith’s Seafood Shack: The sashimi and lobster rolls alone are worth the trek to this no-frills, cliffside haunt near the Gay Head Lighthouse, complete with knockout ocean views. Aquinnah. $$
Three places to go after dark.
At the bi-level Alchemy, the steak frites and fried risotto balls don’t distract from the tropical drinks such as tangy mojitos and gin-and-juices. Edgartown; 508/627-9999.
Peanut shells blanket the floor at the laid-back Offshore Ale Co., a neighborhood pub that stays packed until the wee hours. Try the Offshore Amber Ale—it’s brewed on site. Oak Bluffs.
A snug, railroad-style lounge, Sidecar Café & Bar draws crowds with its innovative cocktails, including the Brown Chicken, Brown Cow, made with Domaine de Canton ginger liqueur, Wild Turkey American Honey liqueur, and ginger ale. Oak Bluffs.
Restaurant Pricing Key
$ Less than $25
$$ $25 to $75
$$$ $75 to $150
$$$$ More than $150
Hopscotch across the island for ocean-themed mementos, one-of-a-kind glassware, and more.
Midnight Farm is a browser’s paradise of funky furniture and unique finds—quilts from India, jars of homemade mango-lime salsa, and kitchen chairs with denim covers. Vineyard Haven.
Interior designer Liz Stiving-Nichols hand-selects each piece at Bespoke Abode, from driftwood picture frames to porthole mirrors and stools. Her Townie Pillows, stamped with Vineyard town names and zip codes, are an island favorite. Vineyard Haven.
If you’re looking for nautically inspired gifts, head to AquaNaut Gallery. Many of the intricate watches (decorated with ships and lighthouses), scrimshaw knives, and shadow boxes inlaid with seashells are made by island craftsmen. 76 Main St., Vineyard Haven; 508/687-9865.
Opened in 1858, Alley’s General Store is a throwback to an era when every neighborhood had a one- stop shop. Come here for picnic fixings, comic books, and, of course, your morning coffee. 1045 State Rd., West Tisbury; 508/693-0088.
At the light-filled Martha’s Vineyard Glassworks, artisans create colorful vases and tableware. Best bet: the multihued pitchers.
Vineyard Vines pays homage to the island’s preppy heritage with whimsical ties and polo shirts in various pastel shades. Edgartown.
See + Do
Four ways to soak up the Vineyard culture.
The Campground: Hundreds of Victorian gingerbread cottages fill this landmark district, built by Methodists who established camp meeting sites here in the 1800’s. Don’t miss the annual Grand Illumination night (on August 14 this year), when house windows are lit up with paper lanterns. Oak Bluffs.
Island Alpaca: At this seven-year-old breeder’s farm, guests can feed the animals and take them for walks around the 19-acre grounds. Swing by the gift shop for alpaca hats, scarves, and sweaters, all made on the island. Oak Bluffs.
Granary Gallery at the Red Barn: Christopher and Sheila Morse have amassed an impressive and eclectic collection of paintings, sculptures, and photographs by more than 75 international and local artists in their converted barn. The highlights: black-and-white landscape photography by Margaret Bourke-White and Alfred Eisenstaedt. West Tisbury.
Edgartown Lighthouse: The iconic 1881 lighthouse was built for Crane Beach, in Ipswich, Massachusetts; after a hurricane destroyed Edgartown’s original lighthouse, this 45-foot-tall cast-iron structure was dismantled and brought by barge to the Vineyard. Climb the spiral staircase to the top for sweeping views of the harbor and Chappaquiddick. Edgartown.
The Island’s Best Beaches
Hop a ferry to the island of Chappaquiddick, 300 yards off the Vineyard’s eastern coast, for miles of empty sand and great bird-watching (spot blue herons and sandpipers).
West Tisbury’s Long Point Wildlife Refuge encompasses 600 acres of windswept dunes, hiking trails, and unspoiled coastline.
You won’t witness a better sunset than at Menemsha Beach, a two-minute walk from the fishing village of the same name. Pack a picnic and a blanket—it gets cold at dusk.
Three islanders reveal their go-to places.
Author, interior designer, and owner of Midnight Farm
Where I Go For...
Fresh Seafood: Larsen’s Fish Market is a great spot for clams on the half shell and to watch the sunset.
Exercise: To unwind, I love the Bikram yoga at Martha’s Vineyard Hot Yoga (West Tisbury).
Takeout: I’m addicted to kale—and I can always find it on the menu at Scottish Bakehouse (Vineyard Haven).
Executive director, Martha’s Vineyard Preservation Trust
Where I Go For...
An Early Morning Swim: I like taking Mac, my yellow Lab, with me to State Beach at 6 a.m.—it’s the only time we have the area all to ourselves.
Fresh Produce: The fruits and vegetables come straight from the fields at West Tisbury Farmers Market.
Family Downtime: On the weekends, we head to the Flying Horses Carousel. It never gets old.
Chef-owner of Hooked and Atria
Where I Go For...
My Morning Jolt: I start every day with an iced coffee at the lively Espresso Love.
Peace and Quiet: Check out Cedar Tree Neck Sanctuary (Vineyard Haven), the perfect combination of trees, pond, and ocean.
A Late-Night Snack: A lot of chefs go to Smoke ’n Bones (Oak Bluffs). I order a beer and the smoked pig.
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