The Flying Santa tradition traces its origins to a pioneering pilot named Bill Wincapaw. Wincapaw flew amphibious airplanes around the Penobscot Bay region in Maine. He often relied on the area’s lighthouses to get him safely home. To show his appreciation to the lighthouse keepers and their families, on Christmas Day 1929 he loaded his plane with a dozen packages containing gifts for the lighthouse families. He dropped the packages at some of the lighthouses in the Penobscot Bay region.
In the years that followed, Wincapaw expanded the flights to more of the Maine coast and to the other New England states. A few years later the Wincapaw family relocated to Winthrop, Massachusetts. Bill Wincapaw Jr. had a history teacher at Winthrop High School by the name of Edward Rowe Snow, a budding historian. Edward Rowe Snow took an interest in the Flying Santa and took part in the 1936 flights. After some years when the Flying Santa duties were shared by the Wincapaws and Edward Rowe Snow, Bill Wincapaw Sr. died in a plane crash in 1947.
From the Christmas season that year through 1980, Mr. Snow kept the Flying Santa tradition alive. His wife, Anna-Myrle Snow, flew along each year, and their daughter Dolly took part beginning the year she was born in 1951.
Dolly Snow Bicknell has been involved in lighthouse preservation as president of Project Gurnet and Bug Lights in Massachusetts. Dolly has been honored recently with a Keeper of the Light award from the American Lighthouse Foundation, and also a special award from the Hull Lifesaving Museum in recognition of her years on the board of directors of that organization and her work on behalf of many local charities. In this interview, Dolly discusses her personal experience as the daughter of the popular historian and longtime Flying Santa, Edward Rowe Snow, and about her own participation in the Santa flights.
The flights continue today, with Friends of Flying Santa visiting Coast Guard stations by helicopter.
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Jeremy D’Entremont is the author of more than 20 books and hundreds of articles on lighthouses and maritime history. He is the president and historian for the American Lighthouse Foundation and founder of Friends of Portsmouth Harbor Lighthouses, and he has lectured and narrated cruises throughout the Northeast and in other regions. He is also the producer and host of the U.S. Lighthouse Society podcast, “Light Hearted.” He can be emailed at Jeremy@uslhs.org