The organization was the brainchild of William H. Wincapaw, a floatplane pilot from Friendship, Maine. He was well known for transporting passengers and cargo along the Maine coast. He frequently took to the air in less than ideal conditions to provide transport for sick or injured islanders. His actions were responsible for the saving of many lives. On many of these flights, his only means of navigation were the lighthouse beacons maintained by keepers along the coast. He had a great deal of admiration for these men and their families and felt that something special should be done to show them how much their efforts were appreciated. On December 25, 1929, he loaded up his plane with a dozen packages containing newspapers, magazines, coffee, candy and other items - 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. So well received were his Christmas gifts, he expanded the program to cover more light stations and Coast Guard stations throughout New England. Wincapaw did not initially consider himself a Santa Claus; the title was bestowed upon him by residents of the stations that he visited. Soon he was joined on the route by his son, Bill Jr. , and by noted author Edward Rowe Snow. Snow participated in the program for over forty years before his retirement.
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