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A shingled house on the dune at Menemsha as the sun goes into the Sound. This is the light Alfred Eisenstaedt came back for every August for half a century, and the reason the Menemsha Inn keeps a room in his name.
Who summered where on Martha's Vineyard, and what a visitor can actually see: Eisenstaedt's Menemsha, Benton's Chilmark, Cronkite's Edgartown harbor, Styron and Buchwald in Vineyard Haven, McCullough and Katharine Graham in West Tisbury, Belushi's grave at Abel's Hill, and the Onassis farm in Aquinnah that opened to the public in 2025. Public places named, private homes left alone.
Martha's Vineyard is famous partly for who kept coming back. A president's widow bought a farm above the cliffs; the most trusted man in America moored his ketch in Edgartown; the century's great photojournalist died in a Menemsha cottage he had rented for fifty Augusts; a Pulitzer novelist wrote in longhand behind a Vineyard Haven house; a comedian is buried by a Chilmark road with beer bottles on the stone. Visitors ask about these people constantly, and the island's answer is a shrug, because the whole point of the place was that nobody bothered them. This guide honors that. It tells you who summered where, town by town, and it separates the places you can actually stand in, a gallery, a cemetery, a public reservation, an auction tent, from the houses that are still somebody's home and are not on any map of ours.
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Alfred Eisenstaedt first came in 1937, a young Life photographer on assignment, and said the Gay Head cliffs reduced him to tears. He came back every August for the rest of his life, took the Pilot House cottage at the Menemsha Inn, walked the up-island roads with a camera, and died in that cottage in August 1995 at 96. In between he photographed the island the way he photographed everything: a ferry breaking through harbor ice in 1961, the Gazette's pressroom in 1952, a Wampanoag schoolteacher in Aquinnah, Walter Cronkite on the Edgartown Yacht Club tennis court in 1975, a president on vacation in 1993, a crooked oak in West Tisbury he made locally famous. The Granary Gallery in West Tisbury gave him his first show in 1986, became his island living room, and still carries close to a hundred of his prints; the Martha's Vineyard Museum built a summer exhibition around him in 2024 from its own collection and his recorded voice; the inn keeps his portrait over a bookcase in the Eisenstaedt room. Thomas Hart Benton got there first: the Missouri painter spent his first summer in Chilmark in 1920 and about fifty more, and his Vineyard pictures of fishermen, dunes and farm people are in the Granary's back rooms and in museums from here to Kansas City. His 1926 portrait of George and Sabrina West, an elderly deaf farm couple from Chilmark, hangs in the Whitney Museum in New York as The Lord Is My Shepherd; it is the island's famous deaf community, the one that grew its own sign language, sitting for a painter. Benton's student Jackson Pollock spent the summers of 1934, 1936 and 1938 with the family in Chilmark, sleeping in a converted chicken coop and doing more clamming, woodcutting and house-painting than art. Both are in our galleries guide; the light they chased is in the photo spots guide.
Gay Head Light on its moved footing at dusk. The cliffs below it are the view that undid Eisenstaedt in 1937; the farm along the pond behind it was the Onassis place, and since 2025 most of it is yours to walk.
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The island's famous people came here because a lobsterman would not look up when they walked past, and that bargain is still in force. So this guide names what is open to everyone, the Gazette, the galleries, the cemetery, the auction tent and the reservation, and leaves the houses on writers' row, on Green Hollow, on Music Street and by the pond in Aquinnah as what they are, somebody's home, without addresses. A familiar face at the farmers market gets a nod here, the same as anyone. The Jaws tour is the one outing on the island where the famous are the actual program.
| Menemsha | Alfred Eisenstaedt, 1937 to 1995, Menemsha Inn; Granary Gallery prints; museum collection |
|---|---|
| Chilmark | Thomas Hart Benton from 1920; Belushi and Hellman at Abel’s Hill; Possible Dreams at Allen Farm |
| Aquinnah | Red Gate Farm, now Squibnocket Pond Reservation (public since June 2025) |
| West Tisbury | David McCullough on Music Street; Katharine Graham’s Mohu (private) |
| Vineyard Haven | Styron, Buchwald, Wallace, Carly Simon; Possible Dreams founded here in 1979 |
| Edgartown | Walter Cronkite and Wyntje; the Gazette under the Restons 1968 to 2010 |
| Oak Bluffs | Dorothy West, Shearer Cottage, the Obamas and the Clintons on vacation |
Eisenstaedt’s island years, the Pilot House, his subjects and the 2024 exhibition are from the Vineyard Gazette of July 3, 2024 and August 24, 2016 and the Martha’s Vineyard Museum; the Granary’s holdings from the gallery and our galleries guide. Cronkite’s house, boat and books are from the Gazette’s 2009 and 2011 reporting; the Reston purchase and the 2010 sale from the Gazette and the Martha’s Vineyard Times. Styron, McCullough and Graham are from the Gazette’s obituaries and property reporting (2006, 2022, 2001, 2018 and 2019); Possible Dreams from Community Services and the Gazette; Abel’s Hill from the Gazette of September 12, 2019; Red Gate Farm and the reservation from the Gazette of September 2020, September 2021 and June 12, 2025. Benton’s first summer is from the Times’ 2019 exhibition coverage and the artist’s biographers. A 1980 book of Eisenstaedt’s island photographs with text by Polly Burroughs prompted this piece; nothing here is taken from it. The photographs are ours.
No. The houses that are still somebody’s home are not on any map of ours; the whole point of the island for these people was that nobody bothered them. This guide points only to the places you can stand in: a gallery, a cemetery, a public reservation, an auction tent.
The Granary Gallery in West Tisbury, which gave him his first show in 1986 and still carries close to a hundred of his prints, and the Martha’s Vineyard Museum, which built a 2024 summer exhibition around him. The Menemsha Inn, where he rented the Pilot House cottage every August from 1937 until he died there in 1995 at 96, keeps his portrait in the Eisenstaedt room.
Thomas Hart Benton spent about fifty summers in Chilmark from 1920; his 1926 portrait of George and Sabrina West, a deaf Chilmark farm couple, hangs in the Whitney in New York. His student Jackson Pollock spent the summers of 1934, 1936 and 1938 with the Bentons, sleeping in a converted chicken coop.
A president’s widow bought a farm above the cliffs, Walter Cronkite moored his ketch in Edgartown, a Pulitzer novelist wrote in longhand behind a Vineyard Haven house and a comedian is buried by a Chilmark road with beer bottles on the stone. The guide goes town by town.
From Chilmark’s famous deaf community, which grew its own sign language; Benton’s deaf farm couple sitting for a painter is that community on a museum wall.
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Oak Bluffs or Edgartown: where to stay on Martha's Vineyard, compared on the ferry (the summer boat lands in Oak Bluffs), room rates ($200 to $400 vs $250 to $450 in August), nightlife (Circuit Avenue to 12:30 vs a 10 PM bylaw), restaurants, beaches, parking, children and couples, with the honest middle answer.
Joshua Slocum, first to sail alone around the world, spent his last years farming in West Tisbury and vanished from Vineyard Haven harbor in November 1909. The voyage, the farm called Fag End, the last departure, and what a visitor can actually see: the harbor, a marker stone by a country road, the museum's Slocum papers, and the book itself.
The red bus that gets the loudest cheer in the Edgartown Fourth of July parade belongs to Camp Jabberwocky, a tuition-free summer camp for people with disabilities that has run on the Vineyard since 1953. An islander's account of where it came from and what it is. For anything official, the camp's own site is the source.
The Feast of the Holy Ghost in Oak Bluffs, held every third full weekend of July since 1928: the Queen Isabel legend behind the free soup, the Sunday parade from the ferry up Circuit Avenue, the crown blessed at Our Lady Star of the Sea, the sopas at the Portuguese-American Club, the club the rest of the year, and how a visitor should behave at the island's Portuguese feast.
The words you will hear on Martha's Vineyard and what they mean: up-island and down-island, on-island and off, going to America, the boats, wash-ashore versus native, Five Corners, the Triangle, the Blinker, Chappy, OB, the Campground, the Derby, the Fair, island cars and the Vineyard shuffle, with pronunciations.
East Chop Lighthouse in Oak Bluffs: the 1878 cast-iron tower on Telegraph Hill, the Sunday sunset openings run by the Martha's Vineyard Museum, the semaphore and Chocolate Lighthouse history, and the bus stop and parking below the hill.
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