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Rare Photos of the Kennedy Family Compound in Hyannis Port
The history of the estate dates back to 1928.
When the Kennedys needed to get away from the hectic world of politics for some peace and quiet, there was one place they always went to: Hyannis Port, Massachusetts. The Cape Cod destination has a rich history that first began in 1928, when John F. Kennedy's parents purchased a family home in the area. After JFK, his brother Ted, and his sister Eunice purchased the three surrounding estates, the Kennedy Compound was officially born.
It was at his childhood summer home that the future president—then just 11 years old—learned to love the water. Sailing and swimming along the Nantucket Sound was a beloved annual tradition that was passed on to future generations. To the Kennedys, the area has always been more than just a vacation spot—it's a place of comfort. It was also the unofficial base for JFK’s winning 1960 presidential campaign, and where his family went to grieve his assassination only three years later.
There have been marriages, family reunions, presidential meetings, and many more memorable moments at Hyannis Port over the years. Though you can't see the Kennedy Compound unless you're on a private boat, walking tour, or a museum visit, these snaps offer a glimpse into what life looked like inside the exclusive retreat years ago.
The Kennedys pose outside their Cape Cod getaway during Thanksgiving in 1948. Twenty years earlier, Joseph and Rose Kennedy purchased the cottage they had been renting for two summers. They immediately got to work enlarging and remodeling it to make space for their nine children, and in a matter of no time, transformed it into the sprawling property it is today.
John F. Kennedy and four of his eight siblings—Jean, Pat, Robert, and Eunice—review one of his senate campaign brochures in Hyannis Port. Their mother made sure to decorate both for livability and style. Bob Luddington, who helped design the home, told Boston.com: "She was particularly, shall I say, keen on the comfort and the flexibility of the furnishings, so that they would be not only decorative but practical."
Jacqueline Bouvier and JFK smile on the deck of the home shortly after announcing their engagement.
Senator John F. Kennedy relaxes on a floral chair alongside his then-fiancée, as they're interviewed for LIFE magazine in June 1953.
From this angle, the Kennedys' airy windows are on full display. Much of the home is brightly lit, because of the large glass doors and windows that border the rooms.
While preparing for their LIFE interview, JFK and Jackie sit in one of the estate’s living rooms, complete with those same spacious windows and floral curtains. The main floor contained a sun room, living room, television room, dining room, and guest bedroom.
The politician and his fiancée observe a wall of portraits inside the Massachusetts home. Three months later, they would go on to marry in front of hundreds of guests in Newport, Rhode Island.
JFK reads over documents at the desk in his bedroom. His parents' Hyannis Port home meant a lot to the powerful figure. "I always come back to the Cape and walk on the beach when I have a tough decision to make," he once said, "The Cape is the one place I can think and be alone."
From this side, it's easy to spot the future Mrs. Kennedy through what appears to be a connecting powder room. Three years later, John bought his own Hyannis Port estate just two doors down from his childhood summer home. The JFK Library later described it as "the emotional center of the family's life for decades."
JFK, his brother, and his bride-to-be play football outside of the vacation home. Ted Kennedy's annual clambakes were a tradition for the family, who gathered four times a year for the event. In 1958, Ted bought the home between John and their parents.
Jackie Bouvier, Eunice Kennedy, Jean Kennedy, and an unidentified woman chat on the porch. JFK's other half was especially close with his sister, Jean. "Our children were about the same age, so we spent a good amount of time together when she and Jack were living in the White House," Jean once shared with Town & Country. "As much as possible, Jackie wanted her children to have the experience of typical American children."
John and Jackie greet Patricia Kennedy, as she drives up the estate's circle driveway. The home's perfectly sculpted greenery outside the front door makes the entrance even more refined.
After visiting the beach, John and Jackie walk back to the house. Wide windows were purposely installed around the perimeter to take in the picturesque views of Nantucket Bay. A beach shower was also put in at the side entrance to help when coming home after a long day of sand and sailing.
Robert F. Kennedy and his wife, Ethel, play with their children—Bobby Jr., Kathleen, and Joseph—on the floor of the Hyannis Port home. Robert—or "Bobby," as he was often called—bought his brother Ted's property in 1961.
In one of his final weekends at home before hitting the campaign trail, JFK and Jackie take in the ocean view with their daughter. Former Kennedy interior designer and consultant, Bob Luddington, revealed their house (which JFK purchased four years earlier) was known as "the Summer White House."
Later that day, the family takes a walk around the compound grounds. "She's really too little to be aware. She knows there's excitement but she doesn't know why," Jackie told reporters about 2-year-old Caroline, after JFK was named the democratic presidential nominee.
The democratic nominee chats on his outdoor patio with diplomat Adlai Stevenson. It was later discovered that JFK's father, Joe, bought his son and daughter-in-law's house for them, so that there was no bank mortgage. He then gave them a no-interest mortgage for the purchase price, allowing them to save them as much money as possible.
Jackie shows off a copy of The Boston Globe from her husband's presidential election. If the room looks familiar, that's because she took inspiration from Rose Kennedy. Jackie's interior designer at the time, Bob Luddington, revealed to Boston.com: "Jackie was very similar her in her taste level as with her mother-in-law. She liked brighter colors, more contemporary fabrics."
Despite staying busy on the campaign trail, JFK always made time for family. Here, he and Jackie read a story to their daughter, Caroline, on a pink chaise lounge outside of their Hyannis Port home. Years later, in 1986, Caroline held her wedding reception at the special location.
With just months to go before the presidential election, JFK and his running mate, Senator Lyndon B. Johnson, hold a press conference inside the historic Cape Cod living room. Their home was filled with many "early American pieces" and touches of Jackie Kennedy's sophisticated style.
The future first and second ladies of the White House, Jackie and Claudia Alta "Lady Bird" Johnson, attend the same presser in similar polished hairstyles. Jackie's interior designer revealed what it was like collaborating with the style icon, telling Boston.com, "It was a pleasure working with her because she was not hesitant making decisions."
Jackie Kennedy sits with daughter Caroline inside their home for an interview with NBC News' Sander Vanocur. The little details around the room—from the copy of Candidates 1960; Behind the Headlines in the Presidential Race on the bookshelf to the matching floral vase and curtains—were perfectly arranged.
The soon-to-be first family spend election day at the compound, eagerly watching polling results roll in. In 2011, Ted Kennedy Jr. and his wife, Kiki, renovated the "President's House." All the discarded items, from faded wallpaper to window panes, were given to local artists and turned into repurposed pieces. "It became difficult for me to put these pieces of history into the dumpster," designer Mark Grenier shared. The artwork was auctioned off, and the proceeds were used to renovate the John F. Kennedy Hyannis Museum.
A day after the election, the President-elect plays with his daughter outside the sprawling estate. Despite undergoing some renovations over the years, his estate remains true to the character of the original build. Bob Luddington, who helped with a historic preservation project for the home in 2017, praised Ted Kennedy Jr. and his wife, Kiki, for doing "an admirable job" at maintaining the house.
Shortly after his big win, President-elect John F. Kennedy, his wife, Jackie, and his parents, Joseph and Rose, pose for a portrait with rows of golden books behind them.
At the same celebration, JFK's extended family gathers together for a picture. The living room, complete with lit rows of statues, a marble lamp, and dark wooden side tables, is even more visible from this angle.
Even while working, President John F. Kennedy preferred his Cape Cod escape. He invited Russian press to his home for an interview, which he conducted from a wooden rocking chair.
While in Hyannis Port for Thanksgiving, the President invites officials over to discuss military spending. Instead of a White House boardroom, the group plans the defense budget in cozy living room chairs surrounded by floral decor.
The first family lounges on blue outdoor furniture with some furry friends. Despite being allergic to dogs, JFK loved animals and wanted his children to experience the joy of having pets. His favorite dog was Charlie, a Welsh terrier gifted to him by his wife during his presidential campaign.
In one of his final interviews, JFK sat down with CBS's Walter Cronkite at his Cape Cod home. The interview is both an incredibly revealing and emotional one to look back on, as the anchor asked plenty of questions about Kennedy's plans for 1964 and running for reelection. "I think we will have to wait and see a year and a half from now. A year now," the President said at the time, "It is not that long."
From: Town & Country US