Flying Santa: Over 90 Years of Aviation Magic

Santa doesn’t always fly a sleigh. In a small corner of the world, where the scent of salt rides on December’s harsh ocean breeze, he drops presents from a plane.

While it sounds like something out of a storybook, flying Santa has been around for over 90 years, ever since he began dropping gifts to the isolated families of lighthouse keepers of New England in 1929.

The History of Flying Santa

The lighthouse keepers and their families live remotely on the small, craggy islands off the New England coast. The job of a lighthouse keeper is a vital one, sometimes the only thing preventing a ship in foul weather from dashing itself upon the rocks. Or, in the case of Captain William Wincapaw, a floatplane pilot from Maine, his only means of navigation as he flew along the coast of Penobscot Bay in all kinds of treacherous weather conditions. Unlike Santa, he had no reindeer to guide his flight, only the flashing beacons that the lighthouse keepers kept alight.

Even before Capt. Wincapaw became Flying Santa in 1929, he was undeniably heroic. It was his job to oversee operations of the Curtis Flying Service at the Rockland airfield and the nearby seaplane base. This meant that he frequently braved the elements to transport sick or injured people who lived on the islands.

Over time, he gained a particular appreciation for the lighthouse keepers and their families. Not only did they guide him as he flew, but he also got to know them well. He’d frequently stop on the islands and spend time with many of the families, where he realized that the holidays could be a particularly difficult time to be isolated on the islands.

It was difficult for the islanders to get to stores inland, and many of them subsisted solely on deliveries via ship or airdrop. This meant that access to many luxuries that we take for granted was limited, and around the holidays this became glaringly apparent.

This is where Capt. Wincapaw got the idea of becoming Flying Santa. On Christmas of 1929, he took off with his plane brimming with treats, including candy, coffee, and newspapers, and dropped them to the island families that he appreciated so much.

That was just the beginning. Over time, the project grew, and he recruited his son, Bill Jr., and eventually Bill Jr.’s high school teacher, Edward Rowe Snow, for assistance. The distance that the plane flew expanded to Rhode Island, Massachusetts, and Connecticut, and the number of deliveries that they made increased to over 100 drops.

During World War II, Mr. Snow, along with his wife, Anna-Myrle, kept the tradition alive as the Wincapaws were called to service. When Mr. Snow was called to service himself in 1942, the flights were suspended until 1945, when Mr. Snow return, followed by a 1946 return of the Wincapaws.

After William Wincapaw died in 1947, Mr. Snow and his family expanded the tradition, dropping toys and gifts to even further distances. As Mr. Snow was not a pilot himself, he paid to hire a pilot and a plane every year, and along with New England sponsors, helped to fund many of the gifts.

The Tradition Lives On

Today, the tradition lives on through a non-profit called Friends of Flying Santa. Funded by donations, deliveries of toys and goods are mostly made by volunteer helicopter pilots to Coast Guard Stations. While stops at lighthouses are still made, they’re typically gifts of candy to children.

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