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.