The Flying Santa of New England

Every Christmas, the families of lighthouse keepers along the coast of New England receive presents from a flying Santa Claus, but the jolly old fellow doesn’t come riding in a magical reindeer-drawn sledge but in a helicopter.

The New England tradition of a “Flying Santa” delivering gifts to lonely and isolated lighthouse keepers and their families started over ninety years ago in 1929, when a Maine pilot named Captain William Wincapaw, started delivering gifts for his lighthouse keeper friends in Penobscot Bay in appreciation of the tremendous sacrifices those families made and the difficulties they faced while protecting the coastline and harbors.

Flying Santa plane flies past Boston Light in 1947.

Captain Wincapaw, a native of Friendship, Maine, was a skilled and adventurous pilot who was well known around the Penobscot Bay. At that time, Capt. Wincapaw was overseeing operations of the Curtis Flying Service at the Rockland airfield as well as the nearby seaplane base. His job included flying mail, medicine and supplies to remote coastal communities, as well as moving injured and sick islanders to nearby hospitals. On many occasions during medical emergencies, Capt. Wincapaw took to the air in inclement weather, saving countless lives in the process. During these flights, his only means of navigation were the lighthouse beacons along the coast. Wincapaw had a great deal of admiration for these men and their families who helped keep the lights burning, and thereby keeping the surrounding waters safe. Whenever Wincapaw found time, he would land at a local lighthouse and spend some time chatting with the keepers. This appreciation was mutual. Whenever Wincapaw was flying in bad weather, the keepers kept a watchful eye for his plane. They would always relay word back to the airfield as soon as he had safely passed their position.

In 1929 Wincapaw decided to do something special to show them how much their efforts were appreciated. That Christmas, he loaded his plane with dozen of packages containing newspapers, magazines, coffee, candy and other small luxuries that could make living on an isolated island a little more bearable. He flew to lights around the Rockland area and dropped these modest gifts for the lighthouse families. Wincapaw’s small gesture of Christmas goodwill was so well received by the lighthouse families that he decided to make it an annual tradition, and increased the reach to additional stations all along the New England coast. By 1933, Wincapaw and his teenage son Bill, Jr. who was an aspiring pilot himself, were delivering to as many as 91 lighthouses and Coast Guard stations.

William Wincapaw and his son Bill.

Around this time, Wincapaw was joined by historian Edward Rowe Snow, a high school teacher who taught at the Winthrop High School, where Bill, Jr. studied. Snow was very enthusiastic about the program and agreed to fly some of the routes and deliver packages. When Wincapaw moved to Bolivia to fly gold and mining machinery over the jungles and mountains of South America, it was Snow and Bill, Jr who continued to carry on the tradition.

In 1947, Captain Wincapaw was taking off from Rockland Harbor with a passenger when he suffered a heart attack in the air causing his plane to crash into the ocean, killing both men. After the death of Captain Wincapaw, Snow became the face of the “Flying Santa”. He continued to carry on the now famous tradition of delivering Christmas bundles to stations all along the New England coast, expanding the delivery to 176 lighthouses in 1947. In 1954 he expanded his flights to include Bermuda, the Great Lakes, and a remote location known as Sable Island about 100 miles from Nova Scotia. He arrived near the destination by seaplane, and then took a horse drawn wagon to the lighthouse where he presented gifts to 3 children and 23 grateful adults on the tiny remote island.

Snow continued the program for 44 years before he passed away in 1982 at the age of seventy nine. After his death, the Hull Lifesaving Museum overtook the role of the “Flying Santa”. In 1997, a non-profit called Friends of Flying Santa was founded, and the responsibility of the program was transferred from the museum to it. Today, the gift delivering program is carried out by volunteer pilots to Coast Guard stations and deliver mostly toys and sweets to children.