Pen Bay Pilot: It’s a tradition that began on December 25, 1929, when Capt. William Wincapaw of Friendship [Maine] loaded his plane with a dozen packages containing newspapers, magazines, coffee, candy and other “island luxuries” and flew to the lighthouses around the Rockland area and dropped the modest gifts to the lighthouse families. According to the history of the Friends of Flying Santa, it was Wincapaw’s way of saying thanks for keeping the lights lit so he could find his way through the skies on foggy, foul-weather days.
“Word came back to him in the days that followed that his gifts of Christmas cheer were extremely well received. The keepers and their families were touched to be remembered on this special holiday. A simple gesture of thanks had made the day so much more special for the residents of these isolated outposts. Wincapaw quickly realized that this Yuletide flight deserved to be repeated as well as expanded to include more of the lighthouse families and Coast Guard stations along the coast,” according to the Friends.
Read more about the history of the Flying Santa.