Santa, Lighthouses, and Airplanes: New England’s Flying Santa Tradition

One of my favorite things about working at the State Library is coming across a fun historical fact or story that I had never heard before, while working on something completely unrelated. A few weeks before Halloween I was looking for a book about New England legends in the stacks and came across a book with an eye-catching cover. I flipped through it and while it didn’t have any information I was looking for, I did come across a picture of Santa and an airplane and it made me wonder what the two had in common (this was Santa with an airplane after all, and not a team of reindeer). I took the book back to my desk and started reading and discovered a fun New England story I had never heard about before. If you’re like I was and don’t know the story behind Flying Santa, this blog post is for you!

Image courtesy of Friends of the Flying Santa

The Flying Santa tradition began in 1929 during a harsh winter storm. An airplane pilot caught in the storm used lighthouse beacons along Maine's Penobscot Bay to fly home to safety. The pilot’s name was William Wincapaw of Friendship, ME. To show his thanks to the lighthouse keepers, he dropped packages filled with treats for their families as he flew over the lighthouses. Throughout that year, Wincapaw would get stuck in other storms and the lighthouse keepers would keep an eye out for him, letting airfield know when he had safely passed over their lighthouses. Wincapaw and later his son, Bill Jr., kept this joyous tradition going each year and expanded their Flying Santa trips to also cover Massachusetts, Rhode Island, and Connecticut. The Wincapaws moved to Winthrop, MA in 1933 and by that point, their Flying Santa routes brought them to 91 lighthouses and Coast Guard stations in New England.

William Wincapaw, Sr. (left) and William Wincapaw, Jr. (right)
Images courtesy of Friends of the Flying Santa

Edward Rowe Snow came into the world of the Flying Santa only a few years later. He was born in Winthrop, MA in 1902, and stayed in Winthrop where he became a high school history teacher. In 1936, Rowe Snow, who knew Bill Jr., joined the Wincapaws to assist them with their continuously-expanding Flying Santa program. That first year he covered the 25 southern routes with Bill Jr. flying, while Bill Sr. flew the northern routes.

Image from The Lighthouses of New England, 1716-1973,
by Edward Rowe Snow

Image from The Lighthouses of New
England, 1716-1973, by Edward Rowe Snow

The Flying Santa tradition was carried on by Rowe Snow until 1980. What’s important to note is that Mr. Snow was not a pilot. After the Wincapaws could no longer take part in the tradition, Mr. Snow had to hire a pilot and a plane for the lighthouse flights. He kept this beloved New England tradition going despite the obstacles that stood in his way and despite the funds that he had to contribute to keep Flying Santa alive. After Snow’s Flying Santa days were behind him due to old age, the tradition was kept alive through the work of the Hull Lifesaving Museum and its members, and later with the help of WCVB-TV 5. By 1997, the Flying Santa tradition had expanded so much that it had outgrown the museum. A group of volunteers got together to form the non-profit educational group called Friends of the Flying Santa, Inc. Over the next decade and beyond, many people stepped in to help the Friends keep Santa flying through the New England skies each holiday season.

Be sure to read much more about the history and evolution of this program on the Friends of the Flying Santa website. The full story of this tradition is rich with detail and the Friends have shared lots of photos on their website as well. You can also learn more about this tradition from the New England Historical Society.

Flying Santa in 2022, the tradition's 93rd year. 
Image courtesy of WCVB.

Thank you to the Friends of the Flying Santa for the work they did to document the history of this tradition. It’s a tradition that still lives on today! December 2023 marks the 94th year of the Flying Santa! You can see photos and videos from last year’s flight here. Keep an eye out for photos from this year as well--Flying Santa made a stop at the Hull Lifesaving Museum on Saturday, December 9th!

Jessica Shrey

Reference Librarian