Article

Flying Santa

Boston Harbor Islands National Recreation Area

Captain William Wincapaw started a nearly hundred-year tradition when he loaded his plane with dozens of packages containing items such as newspapers, candy, and coffee, and dropped them off to various lighthouse stations along the coast of Maine on December 25, 1929. Through this well-received gesture to show his appreciation for the lighthouse keepers he frequently worked with, Wincapaw became known as the first "Flying Santa."

By 1933, the Christmas route included 91 lighthouses and Coast Guard Stations across New England. Wincapaw and his family moved to Winthrop, Massachusetts that same year, and the following year William Wincapaw’s son, Bill, became the youngest licensed pilot in the Commonwealth of Massachusetts. Still in high school, Bill became acquainted with teacher Edward Rowe Snow. When the Wincapaws asked Snow if he could assist with the 1936 trips, he accepted. They split the route, with William Wincapaw flying solo, and Edward Rowe Snow accompanying Bill Wincapaw.^[1]

Snow made his first Flying Santa journey alone in 1940, when other obligations did not allow the Wincapaws to participate. Accompanied by his wife Anna-Myrle, they hired an aircraft and a pilot to ensure the tradition continued. In 1941 Snow managed to make several drops. The following year, the tradition came to halt due to wartime obligations.

While Snow had a drop success rate of 90 percent, and carefully wrapped each gift, sometimes incidents occurred. In 1945, the first trip since WWII, the keeper’s daughter on Cuttyhunk Island wanted a doll for Christmas. The package hit a rock on the drop, smashing the doll. Disappointed, the girl cried herself to sleep. Snow made up for the incident the next year by personally delivering a doll to her.^[2]

The Wincapaws rejoined Snow in 1946, and they split up the route again, though this time Wincapaws flew together. In July 1947, Captain William Wincapaw suffered a heart attack while in the air and passed away. Snow took control of Flying Santa.

A man in a santa suit carries presents as he stands on the wings of a plane — "Lighthouse Santa Takes to Air - Edward Rowe Snow, author and lecturer, waves from the wing of his plane as he gets set to take off from Boston."
Boston Globe, December 12, 1948.

In the 1950s, the Snow expanded the route, and in a Coast Guard aircraft managed to get from the East coast to the West Coast. He even added drops in Bermuda. During this time, the flights became a family affair with Edward and Anna-Myrle's daughter, Dolly, joining the operation.

During the 1970s, Snow became concerned for the future of the trips, with his age, flight restrictions, and rising insurance costs. Instead, Snow visited Boston Light, Graves Light, and Coast Guard Stations around Boston Harbor by boat and car. Flight continued to be limited, and Snow retired as Flying Santa in 1981 after a ceremony where the Snow family passed the Santa suit to Ed Mccabe of the Hull Lifesaving Museum, the next flying Santa. Edward Rowe Snow passed away in 1982.^[3]

Staff of the Hull Lifesaving Museum continued the tradition, using helicopters as the primary vehicle for delivery. The route and drop-off points slowly declined due to fewer lighthouses being operated onsite, but the Museum and other community members vowed to carry on to show their support and gratitude for those still operating boat stations and lighthouses. In 1997, a non-profit organization called Friends of Flying Santa was formed to preserve the tradition of the Flying Santa in New England.

Footnotes:

[1] Brian Tague, "History and Origins of the Flying Santa," Friends of Flying Santa, accessed April 20, 2023, https://flyingsanta.org/HistoryOrigins.html.

[2] "Flying Santa Left His Reindeer Behind for These Deliveries," New England Historical Society, last modified 2022, https://newenglandhistoricalsociety.com/stealth-campaign-bring-christmas-tree/; David Kindy, "After 90 Years, the ‘Flying Santa’ Is Still Dropping Gifts from a Plane," Smithsonian Magazine, last modified December 17, 2019, https://www.smithsonianmag.com/history/after-90-years-flying-santa-still-dropping-gifts-from-plane-180973799/.

[3] Tague, "History and Origins of the Flying Santa;" Kindy, "After 90 Years, the ‘Flying Santa’ Is Still Dropping Gifts from a Plane."