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Here comes Santa Claus

It was 1947, and by the time this photo of Maine’s Flying Santa passing Boston light was taken, the holiday flights started by Capt. William Wincapaw were delivering Christmas presents to some 176 lighthouses and Coast Guard stations in New England.

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Wincapaw made a perilous living flying the rugged Maine coast, often coming to the aid of sick or injured lighthouse families. On social visits, he would land at a lighthouse, tie up his floatplane, and trade news and stories with the keeper and his family. The keepers would watch for his plane and call the airfield in Rockland to let them know they’d seen him pass. Just as boats and ships did, Wincapaw used the region’s lighthouses as navigational aids.

Wincapaw decided he wanted to do something special for the lightkeepers. On the morning of Dec. 25, 1929, he loaded his plane with a dozen packages filled with staples for the families and treats for the children. He flew over local lighthouses, dropped the modest gifts and flew home. It was a win-win: The keepers and their families, especially the children, enjoyed the unexpected holiday cheer, and the pilot was touched by their appreciation of such a simple act. The result was that Wincapaw found himself flying again the next year.

By 1933, the Christmas flights covered more than 90 lighthouses and Coast Guard stations. In the ensuing years, the “Flying Santa,” as the press dubbed him, expanded the charitable flights into Massachusetts, Rhode Island and Connecticut, with Bill Jr. and later author and historian Edward Rowe Snow as pilots.

The tradition continues today, thanks to the non-profit Friends of Flying Santa. The annual visits, now done by helicopter, reach more than 1,000 children from over 50 Coast Guard units from Jonesport, Maine, to New York’s Jones Beach. To learn more, visit the Friends of Flying Santa website at

December 2013 issue