Meet the Flying Santas Who Airdropped Christmas Cheer Along the Coast

A Mission of Gratitude

But Wincapaw himself wouldn’t be able to walk over to the Christmas tree and watch his own kids open their presents. No, he had a job he felt necessary – one worth skipping Christmas morning with the family. He was about to embark on a mission of gratitude that would become a tradition that would last over nine decades.

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Source: flyingsanta.com

On December 25, 1929, Wincapaw was on the maiden flight of “The Flying Santas.” Wincapaw, an aviation pioneer, was born in Friendship, Maine, in 1885. Like the Wright Brothers, Wincapaw took to flying airplanes after working at a local bicycle shop. All modes of transportation fueled his curiosity.

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