The Vineyard's Famous Summer People: Who Lived Where, and What You Can Still See (2026)

Cronkite kept a house on Green Hollow from 1974 until his death in 2009 and his 43-foot ketch Wyntje at the dock below it, sailed the Sound for thirty summers, and wrote two books about it with the island painter Ray Ellis. In 1968 James Reston of the New York Times bought the Vineyard Gazette from Henry Beetle Hough and his family owned it until 2010; the paper he bought still comes out from its offices in the village and is where most of our checking starts. Public: the harbour Cronkite sailed, best from Memorial Wharf; the Gazette in print every week. Private: the house, sold by his heirs in 2011.

William Styron rented a house on the harbour in 1959, bought one, and wrote much of Sophie’s Choice in a studio behind it in pencil on legal pads; the harbour houses became known as writers’ row. Art Buchwald and Mike Wallace played tennis together up the hill, and Buchwald founded the Possible Dreams auction in 1979 and hosted it as a cowboy-hatted auctioneer for 28 summers; it still runs every August for Martha’s Vineyard Community Services, with a celebrity host, and anyone can buy a ticket. Carly Simon started singing here as a girl and lives here year-round. Public: the harbour walk to Owen Park, the auction, the Playhouse. Private: every one of the houses.

David McCullough moved to Music Street in 1972 and wrote most of his books, Truman and John Adams among them, in an eight-by-ten shed in the back yard until his death in 2022. In the same year Katharine Graham of the Washington Post bought Mohu, 218 acres at Lambert’s Cove, because Henry Beetle Hough begged her to save it from developers; her family sold the last of it in 2019 for a record $32.5 million. Public: the Granary Gallery, Alley’s porch, the Ag Hall. Private: Music Street and Mohu both. Earlier still, Joshua Slocum farmed here from 1901 until he sailed out of Vineyard Haven for good in 1909; his story is its own post.

Benton’s fifty summers are above. At Abel’s Hill Cemetery on South Road, a cemetery four centuries old, John Belushi’s stone stands by the entrance (moved there with his widow’s permission when fans wore a path through the older graves), a boulder up the path reads BELUSHI, and visitors leave beer bottles, coins and quotes; Lillian Hellman’s grave a few rows on collects coins. Public: the cemetery, free and open. James Taylor lives up-island and plays the island now and then; where, is not our business.

Mrs. Onassis bought Red Gate Farm, hundreds of acres between Squibnocket Pond and the ocean, in the late 1970s, and her family kept it for forty years. In 2020 the Land Bank and Sheriff’s Meadow Foundation bought 304 acres of it for $27 million, added 32 more in 2021, and in June 2025 opened it as the Squibnocket Pond Reservation: a north trail to the pond and a south trail to the Atlantic beach, with a handful of reserved parking spaces a day in summer. The family keeps 65 acres and the house in the middle, out of sight. Public, at last: most of the land. Private: the house, exactly as it always was.

Dorothy West, Adam Clayton Powell Jr., Paul Robeson and Ethel Waters at Shearer Cottage; the Obamas from 2009 (they bought in Edgartown in 2019); the Clintons in the nineties; Spike Lee in the Highlands. Our Heritage Trail guide and the Inkwell post tell the long version, which is the more interesting one.

Two trails, pond and ocean, on the former Red Gate Farm. Summer parking is by advance reservation, ten spaces at the north trailhead and eleven at the south, on the model of the James Pond preserve; off-season, arrive and walk. No drones, no dogs on the beach in season, and the house is not on the trail.

Open to all, always quiet. The older stones are worth the walk too: the Mayhews, Tiltons and Vincents who made the town.

Eisenstaedt, Benton and a hundred living artists in a restored grain barn, free, open daily year-round, with Friday receptions in summer. The nearest thing the island has to a museum of its famous summer people.

The island’s own collection, in the 1895 Marine Hospital: Eisenstaedt’s photographs and voice, the Benton material, Dorothy West, the Gazette’s history. Exhibitions rotate; the permanent galleries do the island’s whole story.

Buchwald’s auction, 47 years on, at Allen Farm in 2026 with a television host and lots that money cannot usually buy. Tickets on the Community Services site; our events calendar has the date.

Thirty marked sites, beginning at Shearer Cottage, for the community that made Oak Bluffs the most famous Black summer town in America.