Massachusetts is the epicenter of Kennedy legend. President John F. Kennedy was born in Brookline and campaigned from Boston. JFK Jr. grew up in Washington and New York but considered Hyannis Port his summer retreat, where Rose and Joe Kennedy bought their first home in the 1920s. Carolyn Bassette also had ties to the area, having attended Boston University before beginning her career at the Calvin Klein store in Chestnut Hill. After their marriage, the couple returned to the estate many times for weddings, celebrations and relaxing weekends. They found a peace and privacy that was hard to find anywhere else.
Below is a guide to the most important places for families in the Bay State.
Kennedy Compound
The family first lived in a waterfront home in Hyannis Port, and several more homes were built on the six acres as their family grew. In 1957, JFK and Jackie bought their own home for $45,948. John visited there as a child and as an adult, playing with his many cousins and making friends with other kids who lived on Cape Cod. After his mother bought a house on nearby Martha’s Vineyard in 1979, John continued to visit, and after they were married, he met up with Carolyn frequently, hosting dinners and planning renovations on the house.
A view of the Kennedy family’s Hyannis Port estate, which is said to have housed multiple residences for various members of the family.
Hyannis Arsenal
John wasn’t fully present for one of the family’s biggest moments on Cape Cod: On November 9, 1960, JFK gave his presidential victory speech in a former National Guard building, with a pregnant Jackie standing next to him. John, born just two weeks later, made waves. In his closing lines, the new president said, “Now my wife and I get ready for a new administration and a new baby. Thank you.”
Nantucket Sound
The Kennedys’ mansion is on the water, overlooking Nantucket Sound. John owned a small boat where he and his cousins went diving and spearfishing. In 1997, he and Carolyn were spotted kayaking there. Next to the mansion is Eugenia Fortes Beach, named after the civil rights activist who founded the Cape Cod chapter of the NAACP.
John F. Kennedy and Jackie Kennedy at the Hyannis National Guard Armory where Kennedy gave his victory speech after being elected president in 1960.
Four Seasons
This legendary 90-year-old ice cream shop in Centreville was a longtime favorite of the Kennedy family, whose favorite was the peach flavor, and a personal check from the First Lady was long displayed on the wall.
Beachcomber
After graduating from college in 1983, John spent his summers living in a room in a historic house near the site. A White House by the Sea: A Century of the Kennedys in Hyannis Port He spent his summers working on a salvage submersible, searching for rumors of shipwrecks. At night, John and his crew would go to the Beachcomber bar in Wellfleet, where they would dance and go for night swims. John also frequented Joe’s Twin Villas, a popular bar opened by a Cape Verdean in the 1940s in Osterville, near the trails where his grandfather used to ride his horses.
Caroline Kennedy and Edwin Schlossberg were married in 1986 at Our Lady Victorious Church in Hyannisport, Massachusetts.
Our Lady of Victory
In 1986, John was a groomsman for his sister Caroline’s marriage to Edwin Schlossberg at this small Catholic church in Centerville. The dinner and reception, attended by 400 people, was held at the home. Caroline wore a Carolina Herrera dress, and dinner was followed by a fireworks show designed by George Plimpton.
Baxter’s Wharf
This casual seafood spot has long been a Hyannis favorite. The establishment has been owned by the Baxter family since 1919 and has a working pier where you can moor your boat and dine on board. It’s been a restaurant since 1967, and the Kennedy family has been regular patrons ever since.
Jackie Kennedy Onassis on Martha’s Vineyard, home of Red Gate Farm, in 1993.
Red Gate Farm
John spent much time with his mother on their secluded Martha’s Vineyard estate. A former sheep ranch, the property had more than a mile of shoreline and acres of undeveloped land with sand dunes, marshes, meadows, two ponds, blueberry patches, a pool and tennis courts. The landscaping was done by legendary interior designer Bunny Mellon, a friend of the Kennedys, who also had a home on the Cape in nearby Osterville.
Boston University
Carolyn attended Boston University, graduating with a degree in elementary education in 1988. During her time there, she appeared in a calendar called “Boston University Girls” and was in a serious relationship with John Cullen, a member of the school’s hockey team who later played in the NHL.
The house in Brookline, Massachusetts where John F. Kennedy was born was purchased by the Kennedy family in 1966 and is now a museum.
Chestnut Hill Mall
After graduating, Carolyn worked in nightlife and then landed a job at a Calvin Klein store in the suburban Chestnut Hill Mall. Eventually, she caught the eye of executive Susan Sokol, who invited her to work for the company in New York.
83 Beales Street
The Brookline home where JFK was born is a National Park Service historic site. The family moved into the Colonial Revival home in 1914 and lived there for six years before relocating to a larger house a few blocks away. The Kennedys then bought the house back in 1966, allowing people to see the bedroom where the future president was born on May 29, 1917.
John F. Kennedy Presidential Library and Museum
Opened in 1979, the opulent I.M. Pei-designed museum is set on 10 waterfront acres and houses a 30,000-item collection that includes presidential papers, gifts to the president from world leaders, clothing worn by Jackie, and items donated posthumously by Ernest Hemingway. President Kennedy toured the proposed site for the library, then a relatively new concept, just a month before his death.
