Penobscot Bay, Maine
1885 – 1947

International Santa Claus Hall of Fame – December 2016

William Wincapaw had been a pioneer in the early days of aviation and was well known around the Penobscot Bay area of Maine as a skilled pilot. He flew mail, medicine, and supplies to remote coastal communities, and is credited with saving the lives of dozens of men, women, and children over the years.

Lighthouses held a special place in his heart — on more than one occasion, flying through treacherous conditions with little more than dead reckoning to guide him, the beacons along Penobscot Bay had brought him safely home. Knowing the lives of lighthouse keepers and their families were hard, lonely, and monotonous, Wincapaw decided to show his gratitude. On Christmas Day 1929, he loaded his plane with a dozen packages of newspapers, magazines, coffee, candy, and tobacco, and dropped them one by one to the keepers below.

The response was overwhelming. A few days later he spotted a message staked out in the snow — a keeper’s wife had used old newspapers to spell out “Thank you.” Wincapaw vowed to do it again, expanding his route each year until it covered more than 90 lighthouses from Maine to Connecticut. He became known as “The Flying Santa.” After his death in 1947, maritime historian Edward Rowe Snow carried on the tradition, eventually reaching nearly 180 lighthouses and Coast Guard stations. The Flying Santa flights have continued uninterrupted since 1929.