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 goodwill tradition that’s lasted longer than he ever imagined.

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.”

Captain William Wincapaw, photographed in the 1930’s. (Photo courtesy of the Wincapaw family)
Captain William Wincapaw, photographed in the 1930’s. (Photo courtesy of the Wincapaw family)

Born in Friendship, Maine, in 1885, Wincapaw was an aviation pioneer. Like the Wright Brothers, he took to flying after working for a time at a local bicycle shop, as reported in Down East magazine. Transportation, and all its modes, fueled his curiosity. He was a risk-taker, an adventurer, willing to test the limits of man and machine.

Wincapaw earned a living in the skies, first by transporting lobsters and flying seaplane charters. As his career progressed, according to the New England Historical Society, he became a skilled floatplane pilot, carrying mail and supplies to remote coastal communities. Soon he was bringing sick and injured people to safety and helping them find medical attention. He’d fly when others would not, often through storms and heavy fog.

Before the development of sophisticated navigational systems, pilots often relied on the beams from lighthouses to negotiate New England’s rocky coastline and inclement weather. Wincapaw looked to the lighthouse attendants for guidance during tenuous flights, and they never failed him – their beacons gleamed like earth-bound stars through snow, rain and all other adverse conditions.

Over time, he became friends with many of the lighthouse keepers and their families. He appreciated their endless dedication to ensuring the beacons were lit and the surrounding waters were safe. Wincapaw also knew their job was one of isolation and loneliness, as well as one that often went forgotten. The daring Captain wanted to find a way to express his gratitude toward the lighthouse community, and acknowledge their sacrifices. So he packed a plethora of practical gifts – newspapers, tobacco, spices, coffee, candy, soup, and yarn – and small toys for the keepers’ children into his floatplane and took flight on that Christmas morning.

Minutes after takeoff, using a rudimentary compass for navigation, Wincapaw spotted the towering brick construction of the Owl’s Head Light, near the entrance of Penobscot Harbor in Rockland. He maneuvered his aircraft to within a safe, low distance from the lighthouse station and dropped a few of the securely wrapped presents from the plane.

Hearing the commotion outside, a man dressed in flannel pajamas, a heavy coat, and boots rushed from the keeper’s quarters. Keeper Albion Faulkingham waved as Wincapaw circled around the lighthouse several times. He was surprised to see the Captain flying on Christmas morning – and shocked to discover presents on the frozen ground nearby.

Wincapaw flies past the Graves Lighthouse, offshore of Boston, 1937. (Photo courtesy of the Wincapaw family)
Wincapaw flies past the Graves Lighthouse, offshore of Boston, 1937. (Photo courtesy of the Wincapaw family)

After ejecting gifts at eight more lighthouses in the Rockland region, Wincapaw flew home to spend the rest of the day with his family, unaware that his small gesture would leave quite a lasting impression. During a routine flight two days later, Wincapaw spotted the words “Thank You” spelled out in a formation of old newspapers on a lawn near one of the lighthouses. The flight was so well-received that Wincapaw made it an annual event, expanding it to include additional lighthouse outposts and Coast Guard stations along the New England shoreline.

Wincapaw’s son, Bill Jr., an aspiring pilot, later joined his father for the charitable flights. The tandem were dubbed the “Flying Santas” and started dressing for the role in the 1930s, donning red velvet suits trimmed with fluffy white velour under their flight gear, and attaching long whiskers to their chins. The Wincapaw family moved to Massachusetts in 1933, the same year Bill Jr. obtained his pilot’s license, and, according to William H. Wincapaw III – Bill Jr.’s son – by 1937 they were dropping presents to 115 lighthouses and Coast Guard stations in the northeast.

Edward Rowe Snow, left, and two crewmembers prepare for their Christmas flight in 1962. (Photo courtesy of Dolly Snow Bicknell)
Edward Rowe Snow, left, and two crewmembers prepare for their Christmas flight in 1962. (Photo courtesy of Dolly Snow Bicknell)

Eventually the program became too much for the Wincapaws to manage on their own. Even with local businesses donating products to help ease the cost, playing the role of Santa was expensive and time consuming.

Wincapaw Jr.’s high school history teacher, Edward Rowe Snow, would become a quintessential part of the Flying Santa program. An author of numerous books on maritime history, Snow was a huge fan of the Wincapaw’s Christmas flights. He expressed interest in helping with the program, and in 1936 Snow and Wincapaw Jr. – at the time the youngest licensed pilot in Massachusetts – flew to 25 lighthouses and Coast Guard stations across southern New England while Wincapaw Sr. took the northern route.

After accepted a job flying mining supplies and gold over the dangerous jungles of Bolivia, Wincapaw Sr. handed the reins to his son and Snow for 1938. The following year, Captain Wincapaw’s employers flew him back to the United States so he could fulfill his Santa duties. It was, perhaps, the Captain’s most memorable mission – a great reminder of what mattered most. “For the rest of my life, as long as I can fly, I’m coming home to make that trip for those boys,” Wincapaw said at the time, according to Down East.

Captain Wincapaw and his son Bill Jr. in 1946. (Photo courtesy of the Wincapaw family)
Captain Wincapaw and his son Bill Jr. in 1946. (Photo courtesy of the Wincapaw family)

World War II would bring the program to a halt, disrupted by wartime obligations and the fear of being shot down by enemy aircraft. The only Flying Santas flight that Army and Navy officials authorized during the conflict was in 1941, shortly after the Pearl Harbor attack. To minimize risk of it being perceived as an enemy aircraft and shot down, the phrase “CHRISTMAS SEAL PLANE” was scrawled on the side of the Wincapaw plane in two-foot red letters. The flights resumed after the war ended in 1945.

Just two years later on July 16, 1947, Wincapaw Sr. suffered a heart attack while flying his Cub Cruiser seaplane out of Rockland Harbor. He and a young war veteran on board for a scenic flight lost their lives when the plane crashed into the Atlantic Ocean. During his memorial service, foghorns and lighthouse warning bells rang out from Penobscot Bay in remembrance. But the flights didn’t end with Wincapaw Sr.’s passing.

Snow took over the Flying Santa duties, soaring to new heights. With increased support from aviation companies, businesses, and the Coast Guard, he added lighthouses from Canada to the southern United States, and even expanded drops to the west coast. His wife, Anna-Myrle, and their young daughter, Dolly, joined him for the memorable Christmas-day flights.

In 1981, Snow retired from his duties as Flying Santa after 45 years. Today, the Friends of Flying Santa, a nonprofit founded in 1997, continue the annual show of appreciation to Coast Guard personnel and their families. A number of New England helicopter companies have donated pilots to help offset the costs of the flights in recent years. “Without the pilots and their helicopters, we’d be the Driving Santas!” joked Brian Tague, the nonprofit’s president, in a recent interview. He says Flying Santa obligations currently include wrapping, labeling, and bagging gifts for over nine hundred Coast Guard children from 85 different units, and skipping by plane to 31 locations in six states over four days.

Flying Santa posing for a group photo Coast Guard Station Merrimack River, 2009. (Photo by Brian Tague)
Flying Santa posing for a group photo Coast Guard Station Merrimack River, 2009. (Photo by Brian Tague)

“Everyone on the ground gets so happy when you hear the helicopter coming,” says Meghan Deucher, who visits Flying Santa at Pemaquid Point in Maine with her family each year. Usually there is also a place to get hot chocolate and cookies. It’s really such a great program, especially in a rural area.”

In a corner at the Maine Lighthouse Museum in Rockland, a brass memorial plaque hangs on wall. A detailed engraving depicts Wincapaw’s plane flying over Owl’s Head Light. His commitment, which captures the spirit of every Flying Santa and their helpers, is inscribed next to the image:

… dedicated to Captain Bill’s philosophy that lighthouse keepers and Coast Guard crews were true lifesavers and deserved to be recognized for their efforts. With sincere appreciation and respect, we remember this remarkable gentleman as the first Flying Santa of the lighthouses.