Chilmark is about the beach, and about Menemsha. Like the other up-Island towns, the village is small and rural, full of great walking trails and conservation lands. The classic Chilmark day is spent on the beach, followed by a trip to Menemsha to pick up fish or a cooked lobster. Sounds good doesn’t it?

Chilmark Beaches

Squibnocket Beach

Lucy Vincent Beach

Great Rock Bight Preserve

Quansoo Preserve

"Fulling Mill Brook reminded me of Sherwood Forest even though I’ve never been to Sherwood Forest...Just like there’s comfort food, there’s comfort woods."

Shelley Christiansen

"Miles of trails that take you through wet marsh, wooded sections, flat open stretches and then gorgeous rocky coast."

Susan Savory

"Smells from cookouts mingled with salt-spray and the fragrant blooms of wild roses, and at dusk the fireflies twinkled in the sunset over Aquinnah."

Holly Bellebuono


A Brief History

Allen Farm, Chilmark, Horses, Alison ShawLike the rest of Martha’s Vineyard, Chilmark was built more than ten thousand years ago by a conveyor-belt of ice that stretched all the way from the tomato lady’s farm on Middle Road to the North Pole. More recently, Chilmark has earned the distinction of having the highest average property value in the Commonwealth of Massachusetts, and of being the favorite summer haunt of the Obamas. (HillBill went to Edgartown.) The rest, pretty much, is just history.

It’s tempting to imagine leaving the brief history of Chilmark at that, and hitting “Publish,” and watching the clock to see how many seconds ticked by before the outraged phone lines from 508-645-XXXX start ringing off the hook. If you don’t know why, you don’t know Chilmark. Or for that matter, the Vineyard.

For ninety-five percent of the centuries that passed between the Ice and the Obamas, Native people hunted, fished, and watched the Vineyard Sound slowly expand and the Island erode. Then, in 1670, the original English proprietor of the Island, Thomas Mayhew, went to the colonial authorities and got permission to create a semi-feudal fief called “the Manor of Tisbury.” No English lived there at the time, but by 1694 a few families had headed up from (West) Tisbury and split off to create a new town. They were not particularly inventive with their place names, those first Europeans, and they named their new town Chilmark, because that’s the name of the town next to the original Tisbury, back in England. Perhaps nostalgia ran in the family.

Deafness definitely did. Two hundred years later, in the 1860s, Chilmark was most well-known for the number of citizens who were born without hearing and who couldn’t tell you in one paragraph whether their father was also their second cousin once removed, or their first cousin twice removed. American sign language, some say, was heavily influenced by the Island’s home-grown sign language. (How do you say two lobster rolls and a pint of clams in sign language?)

Speaking of lobster rolls and clams, Chilmark has always had a kind of split personality, between the stone walls and sheep pastures along South and Middle Roads and the fishing village of Menemsha. The sheep pastures were known for sheep, not surprisingly, and during the Revolution the British requisitioned ten thousand of them in an action now called “Grey’s Raid.” The Menemsha fleet was best known in its heyday for its sword fishing prowess: the fish were harpooned from the bowsprit of sailing vessels. Overfishing by factory boats and longliners has decimated the swordfishery, but the art is not entirely lost.

For visitors, Chilmark today is mostly known as the land of expensive summer rentals, exclusive private and town beaches, and sunsets at Menemsha. And a recent Hollywood invasion. But year round, the farmers still farm, the sheep still bleat, and the fishermen still fish. In recent years some of the fishermen are even farming: oysters, that would be.

“Settled”: 1660

Incorporated: 1694

Land Area: 19.1 square miles (49.6 km2)

Water Area: 81.3 square miles (210.5 km2)

Population: 843

Getting Around

Photo by Ralph StewartYou won’t find any car, bike, or moped rental shops this far up the Island, so plan accordingly. The heart of Chilmark is windy, rural, sometimes even dirt roads, so the best way to get around is via car, bike, or, since Chilmark is brimming with walking trails, by foot.

The Vineyard Transit Authority busses will pick you up or drop you off wherever you want, but the smartest place to hail one is either from Menemsha, or the Chilmark Store.

Where to Stay

Ralph StewartLodging in Chilmark comes with the much coveted sticker to private beaches Lucy Vincent and Squibnocket. That’s not the only reason visitors seek out Chilmark — for one reason or another, Chilmark has always been the town of choice for President Obama and family.

Chilmark has rental homes galore, for a price, and a few key hotels, inns, and B&Bs that have made a name for themselves nationally, including the Beach Plum Inn, the Menemsha Inn, and the Captain Flanders House.

Milk, Cash, Etc.

Chilmark StoreFor essential goods in Chilmark, just decide which hub you’re closer to: The Chilmark Store, or the village of Mensemsha. The Chilmark Store has a mini grocery, lots of dry goods, and a pretty good racket for sandwiches and pizza by the slice. You’ll find an ATM next door at the Martha’s Vineyard Savings Bank.

If you find yourself on the Menemsha side of town, you can pick up some stand-by items at the Menemsha Market. Or, there’s an ATM, newspapers, and snacks at the Texaco station. You’ll find public bathrooms here too, at Dutcher’s Dock.

See & Do


Don’t tell the other towns we said so, but Chilmark just may be the ultimate outdoor town. It has the most extensive network of Land Bank trails, looping around almost the entirety of the town. Lucy Vincent Beach is considered by many the most beautiful beach in America, and Squibnocket beach is considered by many the most primo surf spot on the East coast, brah.

Then there’s Chilmark Pond for kayaking, Menemsha village for fishing, and … are you still inside? In the words of wise mothers everywhere, go outside and play!

Arts & Culture

cinema circus 2.JPGWhat Chilmark lacks in commercial venues for the arts, it makes up for with a deeply seeded, cultural appreciation for all things artistic. This is a town where, no joke, the bank doubles as a gallery for local artists.

Chilmark is also the only town with its own community center, where year-round, the humble people of Chilmark gather for potluck suppers, authors’ talks, and live music.

A few galleries have worked their way this far up-Island, including the Kara Taylor gallery, which showcases the artist’s unique, nature inspired oil and mixed media paintings.

And if you hear strange drumming from the beach at night, well, that’s just Chilmark.


Photo by Lynn ChristoffersThe shopping in Chilmark is mostly limited to Menemsha Village, where, tucked among the lobster shacks, you’ll find clothing and jewelry shops, and one of the coolest old Antique vendors on the Island.

Groceries and essentials can be purchased at the Chilmark Store or Menemsha Market (see Milk, Cash, Etc.)

If you’re looking for a fantastic Island gift (that doesn’t need to be non-persihable) stop in to Chilmark Chocolates. Just be careful who you get hooked: families of Islanders have threatened to cancel Christmas if their annual box of Chilmark Chocolates does not arrive.

Eat & Drink

The Bite RestaurantYou have a few great options when it comes to sit down restaurants in Chilmark. There’s the Chilmark Tavern, which puts a contemporary fusion twist on family-friendly pub food, and the Home Port, a seafood and steak based  restaurant with a take-out window. The Beach Plum restaurant at the Beach Plum Inn is open for brunch.

But the real heart of Chilmark dining is in it’s take out spots. In Menemsha village, folks load up on Lobster and chowder from Larsen’s to sit on the beach and watch the sunset. Or otherwise, they stock up on fish sandwiches and fried oysters from the takeout window at The Home Port, or burgers and soft-serve from The Galley. You get the picture: you don’t want to be stuck in the back corner of a crowded restaurant when the sun goes down over Menemsha Bight.