While digitizing the logs of The Graves Lighthouse in Boston Harbor, I noticed several entries about packages being dropped from an airplane. The keepers at this offshore station considered this a noteworthy event and probably appreciated some Christmas cheer while separated from their families during the holiday. (The Graves was what was called a “stag station” — there was no accommodation for families.) In future years the log identifies the pilot as Capt. Wincapaw, who started the Flying Santa tradition.
In the early days of aviation, pilots, like mariners, often used lighthouses to track their location. Lacking sophisticated navigational equipment, they sometimes relied on lighthouses to set their course in stormy or inclement weather. One such pilot, Captain William H. Wincapaw, a native of Friendship, Maine, flew a variety of aircraft, including amphibious planes around the Penobscot Bay area. In 1929, Captain Wincapaw, flying blind in a snowstorm and low on fuel, spotted the gleam of Dice Head Light, which led him safely home. To show his appreciation he dropped gifts to light stations in the Rockland area and began the tradition of the Flying Santa.
The packages containing newspapers, magazines, coffee, candy, and other items were so well received and the keepers and their families so appreciative that Wincapaw expanded the tradition to include light stations not only in Maine, but all over New England. In 1938 Edward Rowe Snow took over job and continued delivering packages until 1980. Today the Friends of Flying Santa continue this tradition of showing gratitude to modern-day Coast Guard personnel and their families.
Note that some of this text is excerpted from my book Maine Lighthouses: Documentation of Their Past.