The Flying Santa tradition traces its origins to a pioneering pilot in Maine named Bill Wincapaw. To show his appreciation to lighthouse keepers and their families, on Christmas Day in 1929 he loaded his plane with a dozen packages and dropped gifts for the lighthouse families in the midcoast area. He soon expanded the flights to more of the Maine coast and to the other New England states. Edward Rowe Snow, a teacher and budding historian in Massachusetts, became interested and took part in the 1936 flights. Edward Rowe Snow kept the Flying Santa tradition alive through 1980, flying over the lighthouses of New England and sometimes traveling as far as the West Coast.
Edward Rowe Snow’s daughter Dolly flew on her first Flying Santa flight when she was less than one year old, and flew yearly for decades after that. This interview is an edited version of the one that was first heard on the podcast in December 2020. Today, the Flying Santa flights are carried out by helicopter by the nonprofit Friends of Flying Santa as a show of gratitude to Coast Guard personnel and their supportive families.
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U.S. Lighthouse Society Historian Jeremy D’Entremont is the author of 24 books and hundreds of articles on lighthouses and maritime history. He is a past president of 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’s weekly podcast, “Light Hearted.” He can be emailed at Jeremy@uslhs.org