The Flying Santas Who Airdrop Christmas Cheer to America’s Lighthouse Keepers

When a 1920s aviation pioneer launched a thank-you project for the families that keep coastal ships safe, he propelled a tradition that’s lasted longer than he ever imagined.

Photo courtesy of the Wincapaw family

Christmas Morning, 1929. Rockland, Maine, airfield — not one speck of snow danced in the calm breeze. For miles, blue heavens lined the clear horizon. Captain William Wincapaw checked the gauges on his single-engine floatplane and inhaled deeply. After a flip of a switch, the propellers began to whirl. Across the seats behind him, a dozen festively wrapped presents awaited their special delivery. Wincapaw, his cheeks rosy from the nippy air, smiled as he glanced at the assembly of Yuletide spirit bouncing in tune with the motorized beat of the engine. As the plane caught altitude, families along the northeast coastline were just beginning to stir. Soon they’d circle around decorated trees, exchange gifts, and turn small moments into treasured memories.

But Wincapaw would not be among them. Instead, he embarked on a mission of gratitude that to his pleasant surprise turned into an 87-year tradition. It was the maiden flight of “The Flying Santas.”