The Flying Santa

In 1929, a Maine lighthouse Christmas tradition began after pilot Bill Wincapaw delivered mail and supplies to island communities. Caught in a severe winter storm, he spotted the Dice Head Light in Castine which reoriented southward headed using seven other lighthouses to guide him safely home to Rockland. In gratitude, he loaded his plane with Christmas presents and air-dropped them to the families of the lighthouse keepers – a tradition that continues today by the Friends of Flying Santa. In 2023, his Maine stops are scheduled for the last weekend in November. (

Photo Credit: Brian Tague