Captain William Wincapaw, an ace float pilot from Rockland, Maine, started the Flying Santa program in 1929. The lighthouses were vital navigational aids as he transported goods and ferried sick or injured islanders. Moved to do something special for isolated keepers and their families on Christmas Day, he dropped packages containing coffee, magazines, candy, and a few toys to 12 wind-swept lighthouses in Maine’s Penobscot Bay. Word of the surprise holiday deliveries spread quickly as the keepers and their families were deeply touched by Wincapaw’s gesture. During the next several years, his drops expanded down the coast to Connecticut. By the time he moved his family to Winthrop, Massachusetts, in 1934, he and his son Bill—at 16, the youngest licensed pilot in the state—were dropping presents to more than 90 lighthouses. They soon recruited Snow, Bill’s ebullient high school history teacher, to help with the flights. Upon Wincapaw’s death in 1947, Snow carried the Flying Santa tradition forward for more than three decades.
Marla Rogers was the youngest of lighthouse keeper Archford Haskins’s seven children raised at Great Point and Sankaty Head Lights on Nantucket, and Owl’s Head Light in Maine. The first time she heard the roar of Snow’s plane, she thought it might be crashing. “It was flying really low. I remember the family running out to see the plane circling the lighthouse, then [Snow] throwing a package out. It was really exciting, especially when we opened the bundle and saw presents for each child!” The packages were full of hand-knit mittens, Snow’s latest book, and a puzzle, game, or treat. “The treats were a big deal,” says Rogers. “We never got sweets. Cake and fudge were on birthdays only. The first time I ever ate a Ritz cracker was when we moved to Sankaty Head!”