Some cruising destinations stand the test of time with generations of boaters. Among them is Cuttyhunk, Massachusetts.
Surprisingly, Manhattan earns a mention in the history of this outermost of the Elizabethan Islands. “The island really began as a fishing destination for bigwigs in New York City,” says Robyn Weisel, director of the Cuttyhunk Historical Society. “Businessmen came out to the island looking for striped bass. There was a fishing club, and it still exists today.” Cuttyhunk was, and is, beloved because it’s kind of incognito, she says. “Even people who live seven miles off the coast in New Bedford don’t know where Cuttyhunk is.”
U.S. presidents have come and gone, including Ulysses Grant and Chester Arthur. The latter “was perhaps the most avid angler ever to hold the title of commander in chief,” according to the society’s records. “He visited Naushon and fished from the Cuttyhunk Club for a week in 1882.”
Today, it remains true that having a summer home at Cuttyhunk is a mark of affluence. Unlike in other popular destinations throughout New England, it can be hard to find a rental here. “You have to know a family member or something like that,” Weisel says. But those who visit by boat—she’s counted about 100 vessels in the inner harbor at one time in summer—sometimes get treated to serious celebrity spottings. Back in the day, when the Allen House still served lobster and steak, Jackie Onassis paid the place a visit. Her feet quickly became a hot topic of discussion around town.
“A lot of people on the island don’t wear shoes. Especially residents. It’s kind of like an ‘in’ thing where you can tell the residents apart from the tourists,” Weisel says. “She must have caught onto this trend because she came to the Allen House with no shoes on—but it was the one place on the island where you actually had to wear shoes to enter the building. Nobody wanted to be the one to tell her, but somebody eventually went up to her, and she sent somebody out to her boat to go get her shoes.”
Because Cuttyhunk remains so unspoiled it remains a must-stop for boaters cruising around New England, trying to see the best of the best locales. “People think they’re in the ‘in’ group when they come to Cuttyhunk,” Weisel says. “They think it’s a find that not a lot of other people know about. It’s so under the radar, it’s really a boaters’ paradise.”
