The Origin Story...
So the story goes... out of the fog on one stormy afternoon in the late of the 1950s, Spruce Pointers noticed a distressed sailboat limping its way through the high seas toward the resort’s dock. A guest alerted the front desk, the front desk found the activities director, and the activities director tracked down the dock attendant—who had escaped the weather for a matinee at The Strand Theatre in town.
By the time the sailboat finally tied up at the dock, it was John Druce, then in one of his first seasons as owner and manager of Spruce Point Inn, who was waiting to welcome the weary crew. Aboard that boat were two of America’s most famous brothers—Edward “Teddy” and Robert of the politically ascendent Kennedy family. What began as an unplanned emergency landing in rough seas soon grew into a long friendship between the Kennedy family and Spruce Point Inn. Invited in, the crew dried off, warmed up, and unwound in the comfort of the Main Inn for drinks and dinner with the Druces.
Over the years, and into Robert's term as the U.S. Attorney General, the brothers returned to SPI, favoring Starboard, one of our signature waterfront cottages. The cottage is still available to book, and you can even take a virtual tour at the Accommodations section of our website; private, perched with a view of the bay, it remains as timeless today as it was in those summers past. With a sailing reputation that preceeded them, it comes as no surprise that keepers of the SPI lore also recall that the Kennedys made Spruce Point Inn one of their waypoints on summer cruises, and were known to "appear" at the dock from time to time, bringing with them (to the delight of the guests) some of the luminaries of the day who orbited the extended-first family. The Spruce Point Inn archives contain relics from one of these visits, in which we get a glimpse into one of those fabled drop-ins, with astronaut John Glenn, Robert & Ethel Kennedy, singer Andy Williams, and actress Claudine Longet.
JFK in Boothbay Harbor
The Kennedy connection to Boothbay Harbor only deepened when President John F. Kennedy himself came to the region in the summer of 1962. Flying into Brunswick Naval Air Station, Kennedy made his way to the Boothbay Peninsula aboard a Navy PT boat, headed for a weekend retreat on John’s Island, the private property of heavyweight champion Gene Tunney. From the moment he arrived, the visit captivated the entire community. Reports say that as his PT boat pulled alongside the dock it accidentally struck the pilings, leaving a small scar—one that the Kennedys later paid to repair, an early story that locals still repeat with a smile.
On Sunday morning, August 12, 1962, Kennedy attended Mass at Our Lady Queen of Peace Catholic Church in Boothbay Harbor, accompanied by his sister Patricia. Word had spread quickly, and more than 2,500 people crowded the streets and filled the churchyard to catch a glimpse of the President. Inside, parishioners recalled how simply and humbly he participated in the service, slipping into a pew like any other worshipper. The sight of a sitting president in this modest seaside parish was something the congregation—and the town—would never forget.
In between, Kennedy found time to do what he loved best on the water. He sailed aboard the Coast Guard training yawl Manitou, a sleek 62-foot vessel that served as his presidential yacht during the early 1960s. Photographs from the trip show him relaxed and smiling, enjoying the salt air with the ease of someone who always felt most at home under sail. Afterward, he retreated to John’s Island for a quieter interlude away from the crowds, enjoying the pine-lined shorelines that mirrored the New England coastlines of his childhood.
For Boothbay Harbor, the weekend was unforgettable. A presidential visit by water, the quiet dignity of his presence at Mass, and the thrill of seeing the Commander-in-Chief at the helm of a yacht in the harbor—all combined to leave an impression that has lasted more than sixty years. That August weekend in 1962 ensured that Boothbay would forever hold a chapter in the Kennedy story, just as the Kennedys left their imprint on the harbor’s own history.
From stormy seas at Spruce Point to a presidential visit, the Kennedys left behind not just a story or two, but a strand of history that still lives in the imagination of today's Spruce Point Inn!