On Christmas Day in 1929, a pilot from Friendship, Maine decided to make a few airborne deliveries to lighthouse keepers around midcoast Maine to thank them for their service. William (Bill) Wincapaw and his floatplane were well known in Rockport and around Penobscot Bay, as he helped to transport islanders who needed medical help back on the mainland. Wincapaw felt indebted to the lighthouse keepers and their families who made his flights safer as he battled fog and bad weather, so he decided to bring them some simple tokens of his appreciation like coffee, newspapers, and candy. When Wincapaw realized how much this simple act meant to the recipients, he turned it into an annual tradition that would spread throughout New England.
Wincapaw’s son, Bill Jr., eventually joined him on his trips and they expanded their reach to include Coast Guard stations as well as lighthouses and they started to cover the coasts of Massachusetts, Rhode Island, and Connecticut. Eventually, Wincapaw would dress as Santa Claus as he had been dubbed the “Flying Santa” by the lighthouse families. As their reach spread, Wincapaw and his son were able to get businesses to help support the cost of fuel and gifts. He began to bring toys and dolls to the children on his route and continued the tradition of providing coffee, newspapers, and other simple household items that were normally difficult to deliver to the lighthouses’ remote locations.
After the Wincapaws relocated from Maine to Winthrop, Massachusetts, Bill Jr.’s high school history teacher, Edward Rowe Snow, an aviation enthusiast and author of many books about the history of the New England coast, began to help out with the annual Christmas delivery. Father and son would take a northern route, covering Maine, while Snow would deliver to the coast of Southern New England. It continued this way through much of the 1930s. During the war, the 1942 deliveries were cancelled due to the Flying Santas’ military commitments. The following year, the Flying Santas got special permission from military officials to continue their route. They had their aircraft painted with a Christmas slogan to make it clear to the anti-aircraft batteries of New England that they were not an enemy plane.
In 1946, both Wincapaws as well as Snow were back on the job, and they delivered packages to 118 lighthouses and Coast Guard Stations around New England. The following year, Wincapaw Sr. had a heart attack while piloting his plane in Rockport. He and his passenger both died when his plane plunged into the water shortly after takeoff. Edward Snow took over and expanded the Flying Santa route to cover 176 lighthouses and Coast Guard Stations from Maine to Florida.
Snow would continue his deliveries every Christmas for decades (with the exception being 1974, when most visits had to be cancelled due to bad weather). Over the years, as the Flying Santa tradition became more publicized, corporate sponsors contributed aircrafts and gifts and local television stations covered the Flying Santa’s route and deliveries. Snow had to adapt to changing FAA regulations and modernization. He would eventually use a boat to deliver to some islands in Casco Bay and Boston Harbor due to flight restrictions, and when automated lighthouses meant many lighthouse keepers and their families moved away, Snow still made deliveries to islanders and Coast Guard stations.
After Snow’s death in 1982, the Hull Lifesaving Museum in Massachusetts took over the annual flights for several years. Coast Guard members often served as Flying Santas into the 1990s. The route was cut back due to the fact that so many lighthouses were automated by then, but the flights, now run by the Friends of the Flying Santa, continue to take place every year, making deliveries to many of the stops along the New England coast that Bill Wincapaw visited more than 80 years ago.