Gunkholing: Some “Best Of” Days

Cape Cod Life  /  June 2020 /

Writer: Brian Shortsleeve / Photographer: Brian Shortsleeve 

Beach and tidal channel separating Craigville Beach on the right, and Squaw Island on the left. Photo by Brian

In this issue of Cape Cod Life my younger brother, Kevin, has written a fine article about our family’s memorable times at Craigville Beach and Old Craigville Village.

I mentioned recently my father’s fondness for this area and how the whole family recently gathered at the Craigville Retreat Center and celebrated a 100th memorial birthday party in his honor. I promised an article on this subject, please see Pages of History here.

My father was a devoted advocate of Jack Kennedy, and our Craigville Beach Days fondly recall Jack Kennedy being President. Whenever he was in the area crowds always gathered to see him. When he was the Democratic nominee for President, he and his family would go to St. Francis Xavier Church in Hyannis on Sundays. Along with many other fans, we would go to see Jack and Jackie arrive by limo and enter the church through the side door.  

Also, around this time, one Friday evening, Jackie went to the airport in Hyannis to meet a flight and pick up Jack. The press alerted the public and we were there when she arrived. Jackie went up into the control tower and was told Jack’s flight would be about 20 minutes late. She started to depart. My older brother Mike approached her and asked for her autograph. She said, “I’m sorry, not now, sweetie, I’m in a hurry.”

Following his election as President, on Fridays throughout the summer, he would fly to Otis Air Force Base and travel by helicopter to Squaw Island. This flight pattern included flying over the length of Craigville Beach. We would gather on the shore and wave. The pilot sometimes tilted the copter wings from side to side to wave back.

Our family cottage was in a section of West Hyannis Port separated from Squaw Island by a tidal channel and beach. One day my brother, Mike, said, “Let’s go meet the President.” We waded across the channel and walked along the beach on Squaw Island until we reached a tall wooden staircase leading to a house on the bluff above us. At the top of the stairs we started to cross a backyard and a man came out on the porch and said, “Can I help you boys?” Mike said to him, “Is this the President’s house?” He said no and pointed across the street to another house. Mike asked if we could cut through his yard, to which he nodded yes. Then Mike stopped suddenly, and said to him, “Hey aren’t you the President’s little brother?” He answered, “Yes, I am Ted.”  We started to cross the street and were immediately surrounded by a group of secret service agents who made us go back the way we came and get off Squaw Island. It was all Mike’s idea.

A few years later Craigville Beach Association (CBA) held the annual end of season “Race Day” which featured all types of water sport competition including a sailing race. For my second year in a row, I won first place in the sailing race. A few days later a spokesperson for the Kennedy family called Elliot McSwan, the manager of the CBA beach club, and invited all of the CBA Race Day winners to go to Hyannis Port and compete against the Kennedy kids in the same sports. Mr. McSwan said, “No! If the Kennedys want to compete tell them to join the CBA Beach Club like everyone else.” I don’t think Elliot voted for Jack.

My Best,

Brian Shortsleeve, Publisher

Brian Shortsleeve

Brian Shortsleeve is the owner, publisher, and founder of Cape Cod Life Publications. His personal column, “Gunkholing,” has appeared in all issues of Cape Cod LIFE since the very first issue in 1979.