[R]ecently returned from wartime duties at Quonset Naval Air Station in Rhode Island, Captain Bill Wincapaw, wearing the beard, resumed his role as New England’s Flying Santa Claus in December 1946. His son, Bill Jr., right, manned the controls, while Wincapaw, 61, dropped Christmas gifts from the rear of their Douglas DC-3 to 115 isolated lighthouse keepers from Boston to Eastport. Like the Wright brothers, the Friendship native turned to flying from a job in a bicycle shop. He made his living transporting lobsters and flying seaplane charters, and he flew his first Christmas mission in 1929 to thank those whose lights had guided him through fog and foul weather. At each lighthouse, he dropped securely wrapped bundles of newspapers, magazines, coffee, food, smokes, and toys. One year, when he was flying gold and supplies over the Andes for a Bolivian mining company, he made a special trip back to Maine to cover the lighthouse route. “For the rest of my life, as long as I can fly, I’m coming home to make that trip for those boys,” he said at the time.
Tragically, Wincapaw’s 1946 Christmas flight would be his last. The next summer, he suffered a heart attack at the controls over Rockland Harbor. His Cub Cruiser spiraled into the water, killing him and his passenger. Today, volunteers with the Massachusetts-based Friends of Flying Santa organization continue his legacy by helicopter.