Christmas History

New England’s Flying Santa

Flying-Santa-1937In New England, home of hundreds of lighthouses and the families who worked them, there lived a man who in the early 1920s depended upon them in a different way.

The emerging technology at the time was the industry of flight. As one of America’s first pilots, Bill Wincapaw was known around Penobscot Bay for his skill and bravery as a floatplane pilot. The hundreds, if not thousands of islands along New England’s coast, provided plenty of business for the Curtis Flying Service. As a first-of-its-kind service Bill was not only providing flight for cargo between the islands but he often served as an air ambulance in saving the lives of many islanders who needed medical attention on the mainland.

He would often fly, as duty demanded, in adverse weather conditions and he came to depend on the people of the lighthouses even though he sought their beacons from the air instead of from the sea.

It became his habit, whenever opportunity presented itself, to stop at a local lighthouse and spend some time chatting with the keepers. He came to know and love many of these fine people upon whom he depended so much.

He decided in December of 1929 to give back a little and on Christmas day set out in his plane with a dozen packages filled with the stuff of everyday life – things like newspapers, magazines, coffee, candy and other small items. For many people, these were ordinary things but for folks living isolated from the rest of society, where scarcity of these items naturally existed, these items were literally gifts from heaven.

After flying over as many local lighthouses as he could that Christmas Day, Bill returned home to celebrate Christmas with his family, thinking nothing more of his anonymous gesture.

But word of his generosity spread quickly. The gifts from the Flying Santa were all people were talking about. Not only were they surprised, they were grateful. Someone from “out there” had remembered them for Christmas. Bill quickly realized that the flight needed to be repeated and expanded – that Santa needed to visit as many lighthouse families as he possibly could.

Over time, Bill expanded his efforts and brought on elves to aid the Flying Santa in his merry work. Bill Jr. came on board and, due to the notoriety of his flights and his own Christmas spirit, Bill began dressing for the part, Santa’s beard happily flowing in the wind as he leaned over his plane window to drop his packages from his flying sleigh.

By 1933, nearly 100 lighthouses in Massachusetts, Rhode Island and Connecticut were receiving visits from the Flying Santa.

As the effort grew so did the costs. Undaunted, Bill sought out local sponsors who were only too happy to support the folks who helped bring their products to market through the 365-day operation of the lighthouses.

The family effort, with Bill Jr. at age 16 in 1934 aiding in the piloting duties, grew to include Bill Jr.’s high school teacher Edward Rowe Snow, a New England native and descendant of sea captains in his own right. With his background steeped in New England heritage and his work as a teacher and an author, Snow happily engaged in the work of what he was sure was another chapter of New England lore with the Flying Santa. Snow became not only part of the effort, but quite possibly part of the Wincapaw family as well.

As the demands of World War II took Bill and Bill Jr. away from home for military service it was Snow who kept Santa’s sleigh flying. Often taking on the expense of chartering a plane and hiring a pilot, Snow pressed on in remembering the lighthouse folks each season.

The art of Santa delivery is never easily mastered. Everyone knows that Santa has to go down a chimney and often has to fit large packages through tight spaces. But try tossing presents from a plane and hitting the target 100 percent of the time. In the mid-40s Snow started including copies of his many books in the packages and these books would include a self-addressed stamped card that the receiver to put into the mail. Snow did this as a means of tracking how many of his packages were actually received. His return rate on the post cards was 94 percent.

Occasionally, a delivery went a little off target. There were reports of broken car windshields now and then or of fences that sometimes took the brunt of a flying package intended to hit the ground. Usually the gifts were received in good condition but one year Santa received a request for a special doll by a lighthouse family with a little girl who just knew the Flying Santa would deliver. Santa did deliver but the package hit the rocks and shattered the doll. Later the Santa came back in person to deliver the doll as originally promised.

These flights, in Santa suit and all, were not without mishaps. Once Santa lost his beard in a high wind and they were later returned to him in the mail with a note that said “Here are your whiskers, where is our package?”

There are, literally, hundreds of stories of Christmas giving and receiving that have been shared over the years due to the flights of the Flying Santa.

Air transportation has changed over the decades and the evolution of flight has caused for adjustments to be made for the Flying Santa. But for more than 80 years the tradition has continued.

Father of 7, Grandfather of 7, husband of 1. Freelance writer, Major League baseball geek, aspiring Family Historian.

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