Ten Famous Faces: Celebrities Who’ve Called Cape Cod “Home”

Forget Miami Beach or Lake Tahoe – Cape Cod and the Islands have always been known as a playground (or a retreat) to the rich and famous. Celebrities have visited and even purchased homes here throughout history, from actors and politicians to musicians and writers. They come here for a variety of reasons, such as the opportunity to live that Cape Cod experience for themselves, or to seek refuge and peace from their busy lives in the spotlight. Many currently own homes here or have in the past. Here’s just a taste of the famous people who call or have called the Cape “home.”

John F. Kennedy – There is hardly a person in the world who isn’t at least somewhat familiar with the Kennedys, particularly the former president, and their private compound here on Cape Cod. In fact, “Kennedy” and “Cape Cod” have been practically synonymous for decades.

Harry Connick, Jr. – Connick owns a summer home in Chatham, and the singer/actor (and previous American Idol judge) has been seen doing his shopping at farmers’ markets, visiting Four Seas Ice Cream and putting around town just like any other resident.

Meg Ryan – The “Sleepless in Seattle” and “You’ve Got Mail” star has rented a variety of homes on the Cape over the years. Although it seems that she prefers Falmouth, Ryan’s father was a school teacher in Chatham for some time.

The Farrelly Brothers – Writers and directors Peter and Bobby Farrelly are known to own several homes around the Cape. Famous for comedies like “There’s Something About Mary,” “Me, Myself and Irene,” and “Fever Pitch,” among other films, the brothers started their careers as writers on “Seinfeld.”

Carly Simon and James Taylor – Carly Simon and James Taylor were a musical match made in heaven in the 70s, as well as two of the most famous Martha’s Vineyard residents as a couple during their marriage. Since their split in the early 1980s, Simon has made Martha’s Vineyard her ful-time home.

Dan Aykroyd – Actor, comedian, producer, screenwriter, musician and businessman, Dan Aykroyd has owned a home on Martha’s Vineyard for years. The founder of Crystal Head Vodka, Aykroyd famously rode his motorcycle through the streets of Chilmark in 1982 to Abel’s Hill Cemetery, where his friend and fellow comedian John Belushi was being laid to rest.

Tommy Hilfiger – The fashion icon owned a sprawling estate on Nantucket since he purchased it in 1996 for $4.6 million. The Lincoln Circle-area home, called “Point of View,” had 10 bedrooms and eight bathrooms, and 180-degree views of the water. Hilfiger and his wife divorced in 2002 and, in 2013, the ex-Mrs. put the Nantucket home on the market for $27 million, later lowering to $24.9 million.

Robby Benson – This former 1970s and ‘80s heartthrob and Tiger Beat icon has lived the quiet life here on Cape Cod with his family for years. The New York native was the star of such cult classics as “Ice Castles,” “Ode to Billy Joe,” and worked opposite Paul Newman in “Harry & Son.” Benson is now an accomplished author, as well. In 2012, he released his memoir, “I’m Not Dead… Yet.”

Elin Hilderbrand – The “Queen of Beach Reads” is a year-round resident of Nantucket whose romance novels have appeared on the New York Times Best Seller list. All of her novels are centered on Nantucket. She also leads the #mamastrong movement, which supports women who have been diagnosed with cancer. In 2014, Hilderbrand was diagnosed with breast cancer and underwent a double mastectomy.

Taylor Swift – While dating one of the younger members of the Kennedy clan (Conor Kennedy) back in 2012, the “Shake it Off” entertainer bought a mansion within the Kennedy compound itself in Hyannis Port. Not long after, once the brief romance fizzled, T-Swift sold the manse, making a cool $870,000 profit.


About Ann Luongo

Ann Luongo has been writing for Cape Cod and South Shore publications for over 15 years.

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