In 1929 Maine pilot Capt. William Wincapaw started delivering Christmas packages to lighthouses in the Rockland, Maine area with his small plane. He became known as the Flying Santa, and soon expanded his radius.

Boston Light was one of the first lighthouses visited early in the history of the program and is one of the longest-running participants, as most lighthouses in New England have become automated. Today, Boston Light is the only Coast Guard lighthouse with a human keeper, although the light itself is automated.

Throughout the years, the keeper of Boston Light and their family would receive a package dropped or delivered to the lighthouse every Christmas, full of snacks and goodies. The Flying Santa program, now over eighty-three years old, still delivers to Boston Light and has expanded to include Coast Guard stations in New England.