Throughout the history of the U.S. Coast Guard’s aviation branch, service aircraft have come to the aid of the American public in time of need. At other time
s, the holiday season has provided a unique opportunity for private citizens to return the favor.
During the Great Depression, aviator Capt. William “Bill” Wincapaw began the tradition of “The Flying Santa.” Born in Friendship, Maine, Wincapaw oversaw flight operations for the Curtiss Flying Service in Rockland, Maine. He came to admire Maine’s lighthouse keepers and their families for standing the watch in isolated and often inhospitable locations.
To show his appreciation for their dedication and self-sacrifice, Wincapaw decided to deliver gift parcels to local lighthouses on Christmas Day. Early in the morning on Dec. 25, 1929, Wincapaw loaded packages of Christmas gifts into his vintage Travel Air A-6000-A airplane, which featured a single radial engine and wicker seats. That first year, he airdropped Christmas gifts to a dozen lighthouses along Maine’s coast.
Wincapaw continued the tradition the following year. Over time, he came to be known as the “Flying Santa” and the “Santa of the Lighthouses.” He began to dress the part and enlisted his son, Bill Jr., to pilot additional Christmas Day 
flights. His gift parcels included basic items such as newspapers, magazines, coffee, tea, candy, tobacco, soup, yarn, pens, and pencils. By 1933, the program proved so popular that Wincapaw expanded it to include 91 lighthouses from Maine to Rhode Island and Connecticut. He even found commercial sponsors to underwrite the cost of the parcels and the flights.
In the late 1930s, the program expanded, requiring the services of a third Santa. The Wincapaws enlisted New England maritime historian Edward Rowe Snow to fill the position. During World War II, deliveries became more sporadic, and were suspended altogether for security reasons in 1942, the only year the Flying Santa had to stay home. However, by war’s end the Flying Santa had visited an impressive 115 lighthouses and Coast Guard stations. In 1946, the program tested the latest aviation technology, using a helicopter to assist in airborne deliveries. The Flying Santa reverted to fixed-wing aircraft the following year, and helicopters would not be used again for more than 30 years.
In 1947, Wincapaw su
ffered a heart attack during a flight out of Rockland and died in the ensuing crash. Numerous lighthouse keepers, their families, and representatives from the Coast Guard, the Army and the Navy atten
ded Wincapaw’s memorial service. At the appointed time, foghorns and lighthouse warning bells sounded all along Maine’s coast to honor the man who had established the beloved Flying Santa tradition.
After Wincapaw’s passing, Snow took over the program. He and his family became the heart and soul of the operation. With the support of dedicated pilots, Snow honored Wincapaw by expanding the flights to include nearly 180 lighthouses and boat stations. In certain years, the program even served installations along the shores of the West Coast and Great Lakes, and remote Atlantic locations, such as Bermuda and Sable Island, 100 miles off Nova Scotia’s shoreline.
Snow continued the Christmas tradition for 45 years. He retired in 1981, when failing health prevented him from taking part in further Flying Santa missions. That year, oversight of the Flying Santa program passed t
o the Hull Lifesaving Museum, and helicopters replaced fixed-wing aircraft to serve as the Flying Santa’s sleigh.
In 1987, lighthouses underwent automation, but the Flying Santa continued to visit Coast Guard bases and installations. In the 1990s, a number of retired Coast Guardsmen began volunteering to serve as the Flying Santa. In 1997, the all-volunteer Friends of Flying Santa was organized as a private non-profit organization to run the program.
The Flying Santa has been in operation for more than 90 years, since Captain Wincapaw founded it. Today, the program delivers gifts to more than 800 Coast Guard children at 75 units from Maine to New York. The Flying Santa remains a part of Coast Guard legend and the lore of the long blue line.