35 JFK Cape Cod Connections

By Lisa Cavanaugh | Photos courtesy of the John F. Kennedy Library in Boston

Although it was Brookline where John Fitzgerald Kennedy was born 100 years ago on May 29, 1917, he is forever entwined with Cape Cod. There are dozens of places on the Cape and Islands that have been touched by the Kennedy legacy and here are 35 ways our 35th president was Cape Cod-connected:


The Compound: The cluster of white beach houses that have been the secluded summer homes for the Kennedy clan for 90 years had humble beginnings. Starting in 1926, JFK’s family spent a couple of summers in Hyannisport, renting a cottage at 28 Marchant Ave. In 1928, Joseph Kennedy purchased the structure, which had been erected in 1904, enlarging and remodeling it to suit his family’s needs. Jack bought his own house nearby at 111 Irving St. in 1956, and spent time every summer there until his tragic death in 1963.


For generations, the Kennedy family shopped at Puritan Cape Cod on Main Street in Hyannis. When JFK arrived on the Cape, he always changed quickly from his suits into shorts and other casual attire, often purchased from Puritan. Howard Penn, father of Richard Penn, one of the owners of Puritan, took efforts to have JFK made an honorary member of the Hyannis Jaycees in 1960.


As summertime locals, the whole family also frequented the small Hyannis Port News Shop general store and post office on Wachusett Avenue. As a young man, the president’s son, John F. Kennedy Jr., was known to walk or bike through Hyannisport on summer mornings.


JFK loved ice cream and, while it has been rumored that peach was his favorite flavor, he was most often seen enjoying a vanilla cone from Four Seas Ice Cream. Peach may have been Jackie and Caroline’s shared passion because Jackie ordered plenty of it from Four Seas to be served at Caroline’s wedding rehearsal dinner.


When on Cape Cod, the Roman Catholic Kennedys attended Mass at St. Francis Xavier Church on South Street in Hyannis. All the Kennedy boys took turns serving as altar boys and the altar donated by the family in honor of Jack’s brother Joe Jr., who was killed in action in World War II, is still in use today.


In 1960, after Jack Kennedy became president, he and his family regularly attended Sunday Mass during the summer. They always sat in the second row of the East Wing, with their Secret Service detail in the rows in front and behind them. The White House always needed a way to reach the president in an emergency so a “red” phone was installed in the church’s sacristy.


Bobby Kennedy, who was attorney general during his brother’s administration, sat in the west wing of the church and would help with the collections if needed. He was even known to step over the altar rail to serve Mass if the church was short on altar servers.


Jack loved New England clam chowder, preferably made with Cape Cod clams. His regular dining spots included The Captain’s Table at the Hyannis Yacht Club and Baxter’s—restaurants that boasted great views of the water. Baxter’s even allows boaters to dock alongside their outdoor deck and order fried fish and other specialties right on board.


The iconic image of John F. Kennedy on Cape Cod is almost always of him sailing. The young JFK learned how to sail here on a Wianno Senior,  a 25-foot gaff-rigged sloop that was designed in 1913 for a group of sailors from the Wianno Yacht Club in Osterville.


He received his own Wianno Senior, The Victura, in 1933 as a 15th birthday present from his father and it remained his favorite vessel throughout his life. It was the boat on which he taught many others, including his wife, Jackie, to sail.


He and his brother Joe also raced their Star Class sailboats—Flash and Flash II—from 1934 through 1940 with the (now inactive) Nantucket Sound Fleet. In 1934, Jack won the Nantucket Sound Fleet’s Championship Cup.


In July 1941, during the Edgartown Yacht Club Regatta, two young men showed up at the Ocean View Hotel in Oak Bluffs, soaked, barefoot and carrying a torn sail. With no dry clothes and no money, they assured the owner of the hotel that their father would pay for their meal and mending of the sail. They turned out to be Jack and Joe Kennedy.


In 1960, Jackie painted a picture for him, “Welcome Home,” showing The Victura sailing into Hyannisport with friends and relatives welcoming him home.


JFK once said, “I always go to Hyannisport to be revived, to know again the power of the sea and the master who rules over it and all of us.”


When elected President, JFK re-named the presidential yacht Honey Fitz. It was docked on the Cape from his birthday in late May until mid-September each year and he used it every weekend he was there. Named for his maternal grandfather, it was also kept at a slip on the Potomac when he was in Washington and brought to Palm Beach at Christmas. JFK used the boat as often as possible.


He also loved to spend time alone with his children, Caroline and John, Jr.,  on the Honey Fitz in Lewis Bay.


In 1963, on what was to be his last birthday, Jackie threw a party for him aboard the Honey Fitz in Hyannisport.


Everything about the sea appealed to JFK. In the early campaigning days, he and close friend David Powers, who became his special assistant and assistant appointments secretary, used to take the ferry from Boston to Nantucket. That’s not to say that he was unaffected by our sometimes inclement weather, however. One warm winter’s day in Palm Beach, relaxing on the aft deck of the Honey Fitz, Jack turned to Powers and commented, “This sure beats the Nantucket ride, doesn’t it?”


JFK was a habitual doodler and regularly covered sheets of paper with sketches of sailboats, including images of The Victura. His secretary, Evelyn Lincoln, collected and catalogued many of them, which are now part of the collection at the John F. Kennedy Presidential Library and Museum in Boston. 


John Kennedy loved the natural beauty of Cape Cod and one of his favorite books was Thoreau’s “Cape Cod,” which he kept on his bookshelf in Hyannisport next to Rachel Carson’s “The Sea Around Us” and “The Edge of the Sea.”


This affinity and respect for the natural world led him as a U.S. senator in 1959 to co-sponsor the Cape Cod National Sea Shore bill with his Republican colleague, Leverett Saltonstall.


During the 1960 Presidential campaign, JFK advocated saving seashores as wildlife refuges and recreational areas, and he was successful at getting the legislation for the Cape Cod National Seashore passed in 1961. This protected area includes more than 40,000 acres of forest, marshland, bogs and salt ponds along with nearly 50 miles of untouched beach that stretches from Provincetown to Chatham.


To commemorate this achievement, Jackie commissioned a Cape Cod wood carver to create a statue of a shorebird for Jack, which he kept on display in the Oval Office. She also had a sailboat carved in wood, which was kept in the Cape house.


His presidential career was officially launched on Cape Cod and he used the compound as a base during the 1960 campaign. He and his family were in Hyannisport on election day 1960 and at 3 a.m., with results still unknown, he finally went to bed. Later that morning daughter Caroline woke him up by saying “Good morning, Mr. President.”


The now President-elect Kennedy gave his victory speech at the Hyannis Armory on Nov. 9, 1960. The Armory, built in 1958, is located at 225 South St., and hosted Battery D of the 685th AAA Machine Gun Battalion of the Massachusetts Army National Guard.


As much as Jack loved his and Jackie’s house on Irving Street, the Secret Service felt the compound was not secure enough, so the summer White House was moved 1/2 mile away to rented houses on Squaw Island.


JFK conducted many policy meetings at his parents’ Hyannisport home, including a Defense Department budget meeting in their sunroom, and in-person meetings or phone calls with world leaders.


In addition to sailing, JFK enjoyed golf. In fact, Tom Niblet, golf pro at the Hyannis Port Club, would anticipate a call directly from the president to the special phone the White House had installed in the “bag room” as soon as he heard the Marine helicopter fly over the course. JFK made his own arrangements for tee times and would call Niblet and ask: “Tom, are you busy? Get your sticks and we’ll knock it around for a few holes.” Then he would show up carrying his golf shoes, shirt and slacks to get changed in the bag room.


When he arrived by helicopter from Washington, all of the various Kennedy kids would greet him, swarming around him. He was also frequently photographed at the Hyannis Port Club driving a golf cart around full of kids, his own and others.


A new “forever” U.S. postage stamp, commemorating JFK’s 100th birthday, was unveiled on Presidents Day 2017. You can purchase these stamps at the post office on Main Street in Hyannis, next door to the JFK museum.


The John F. Kennedy Hyannis Museum on 397 Main St. features a multimedia exhibit designed to open a window on the days JFK spent on Cape Cod. The museum preserves and promotes the legacy of President Kennedy, his family and their deep connection to Cape Cod.


Overlooking Lewis Bay, the JFK Memorial and Park on Ocean Street was constructed by the residents of Barnstable to honor our 35th president. It overlooks Lewis Bay, where President Kennedy often sailed throughout his life while in Hyannisport. A fountain and wall with the presidential seal and likeness of JFK sits on a rise adjacent to Veterans beach and the Korean War Memorial.


At the Hyannis Youth & Community Center at 141 Bassett Lane, an Olympic-size ice skating rink is dedicated to JFK’s elder brother, Lt. Joseph P. Kennedy Jr., who died in WWII. This facility is open to visitors.


Our 35th president’s passion for Cape Cod was summed up with this famous quote:  “I always come back to Cape Cod and walk on the beach when I have tough decisions to make. The Cape is the one place I can think and be alone.”



A nearly life-size sculpture of John F. Kennedy striding barefoot across sand and beach grass by Osterville sculptor David Lewis graces the front of the JFK Museum on Main Street, Hyannis

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