Massachusetts is central to Kennedy lore. President John F. Kennedy was born in Brookline and ran his campaigns out of Boston. JFK, Jr. was raised in Washington and New York City, but saw Hyannis Port, where Rose and Joe Kennedy first bought a home in the 1920s, as a summer refuge. Carolyn Bessette had her own ties to the area, having attended Boston University before beginning her career at a Calvin Klein store in Chestnut Hill. After marrying they made many trips to the compound for weddings, celebrations, and laidback weekends. They were able to find a degree of peace and privacy that was hard to come by elsewhere.
Below, a guide to the family’s most treasured spots in the Bay State.
The family’s original waterfront home in Hyannis Port spawned several more homes on the six acre property as the family expanded. In 1957, JFK and Jackie brought their own home for $45,948. John traveled there both as a child and an adult, playing with his many cousins and making friends with other children living on Cape Cod. After his mother bought a home in nearby Martha’s Vineyard in 1979, John continued to visit and after his marriage he and Carolyn visited frequently, hosting dinners and planning a renovation of the home.
John wasn’t fully present for one of his family’s biggest Cape Cod moments. On November 9, 1960, JFK gave his presidential victory speech at the former National Guard building, a pregnant Jackie standing beside him. John, who was born only two weeks later, did get a big mention: In his closing line the newly-minted President-elect said, “So now my wife and I prepare for a new administration and for a new baby. Thank you.”
The Kennedy compound was on the water, overlooking the Nantucket Sound. John had a small boat and would go out with his cousins on diving and spearfishing expeditions. In 1997, he and Carolyn were spotted kayaking there. Beside the home was the Eugenia Fortes beach, which was named for the civil rights activist who started the NAACP’s Cape Cod chapter.
John F. Kennedy and Jackie Kennedy at the Hyannis National Guard Armory, where the president-elect gave his victory speech in 1960.
The legendary 90-year-old ice cream shop in Centerville has long been a Kennedy go-to. Their peach flavor was a particular Kennedy favorite and a personal check from the First Lady was long displayed on the wall.
After graduating from college in 1983, John spent the summer living in a room in a historic home near the compound. According to Kate Storey’s White House by the Sea: A Century of the Kennedys at Hyannis Port, he spent the summer working on a salvage diving ship, searching for a rumored shipwreck. At night, John and the crew would hit up Beachcomber, a Wellfleet bar where they’d dance and often end up night swimming. John would also be spotted at Joe’s Twin Villa, a popular bar opened by a Cape Verde native in the 1940s and located in Osterville, near what used to be his grandfather’s bridle path.
Caroline Kennedy and Edwin Schlossberg at their 1986 wedding at the Church of Our Lady of Victory in Hyannis Port, Massachusetts.
John served as best man when his sister Caroline married Edwin Schlossberg at this small Catholic church in Centerville in 1986. The 400-person dinner and reception were held at home. Caroline wore a Carolina Herrera dress and a fireworks show designed by George Plimpton followed the dinner.
The casual seafood spot has long been a Hyannis favorite. The property has been owned by the Baxter family since 1919 and has a working dock that allows boaters to pull and dine on board. It’s operated as a restaurant since 1967 and the Kennedy family have been regulars ever since.
Jackie Kennedy Onassis on Martha’s Vineyard, where her Red Gate Farm was located, in 1993.
John would spend time with his mother at her remote Martha’s Vineyard property. The estate, a former sheep farm, had over a mile of waterfront and acres of undeveloped land with dunes, wetlands, meadows, two ponds, a blueberry patch, pool, and a tennis court. The landscaping was done by Kennedy friend and legendary decorator Bunny Mellon, who had her own home in nearby on the Cape in Osterville.
Carolyn attended BU, graduating in 1988 with a degree in elementary education. While there she was featured in a calendar called “The Girls of B.U.” and seriously dated John Cullen, a member of the school’s hockey team who later had a career with the NHL.
The Brookline, Mass. house where John F. Kennedy was born was bought back by the Kennedys in 1966, and now serves as a museum.
After her graduation, Carolyn worked in nightlife, before taking a job at the Calvin Klein store at the suburban Chestnut Hill Mall. She eventually was noticed by Susan Sokol, an executive who invited her to work for the company in New York.
The Brookline home where JFK was born is a historic site maintained by the National Park Service. The family moved to the colonial revival house in 1914 and lived there for six years before relocating to a larger home a few blocks away. The Kennedys then repurchased it in 1966 so that people would be able to view the bedroom where the future president was born on May 29, 1917.
Set a 10-acre property beside the water, the gorgeous I.M. Pei designed museum, which was opened in 1979, has a 30,000-piece collection that includes presidential papers, gifts given to the president by other world leaders, clothing worn by Jackie, and items from Ernest Hemingway, donated after his death. President Kennedy viewed potential locations for the library, which was a relatively new concept at the time, only a month before his death.
