Cape Cod Life has a great story (with historic B&W photos) on the history of the Flying Santa program. Started in 1929 by barnstorming Rockland, Maine, pilot Bill Wincapaw, the Flying Santas deliver presents to New England’s lighthouse keepers and their families each Christmas. Gifts were originally dropped by plane, but now the program relies on helicopters.
Here’s an excerpt:
The light went out long ago at Seamond Ponsart Roberts’ lighthouse home on Cuttyhunk Island, but memories of her childhood Christmases still sparkle. Like other children of lighthouse keepers sprinkled around remote Cape and Island outposts in the 1940s, she grew up without running water, electricity, or neighbors. She describes the keeper’s house at the west end of the island as “the end of the world,” a place where “visitors were very, very welcome.” Beginning every October, she scanned the sky for the red plane bearing the most welcome visitor of all: the Flying Santa, hero to lighthouse children from Maine to Long Island.