Meet the Flying Santas Who Airdropped Christmas Cheer Along the Coast

It was Christmas morning in 1929 in Rockland, Maine, and there wasn’t one flake of snow as far as the eye could see. For miles, the horizon was clear as could be. Captain William Wincapaw, in his single-engine floatplane, checked the gauges and took a deep breath. With a flip of a switch, the propellers started turning, and Wincapaw peeked behind him.

The Flying Santa plane going passed a lighthouse / Edward Rowe Snow dropping a package

Source: flyingsanta.org

On the seats behind him were wrapped Christmas presents, waiting to be delivered. Wincapaw couldn’t help but smile as he felt the Yuletide spirit in the air along with the hum of the engine. As the plane rose higher, the families in the homes along the Northeast coastline were just beginning to wake up. It was moments away from Christmas morning, every kid’s favorite time of the year. And Wincapaw was about to make it even more meaningful.

This is the origin story of the Flying Santas.

A Mission of Gratitude

But Wincapaw himself wouldn’t be able to walk over to the Christmas tree and watch his own kids open their presents. No, he had a job he felt necessary – one worth skipping Christmas morning with the family. He was about to embark on a mission of gratitude that would become a tradition that would last over nine decades.

William Wincapaw wearing a pilot's hat, jacket, and goggles

Source: flyingsanta.com

On December 25, 1929, Wincapaw was on the maiden flight of “The Flying Santas.” Wincapaw, an aviation pioneer, was born in Friendship, Maine, in 1885. Like the Wright Brothers, Wincapaw took to flying airplanes after working at a local bicycle shop. All modes of transportation fueled his curiosity.

Man and Machine

He was an adventurer and a risk-taker, always willing to test the limits of man and machine. Wincapaw made it so that he could earn a living in the skies. He started out transporting lobsters and flying seaplane charters. According to the New England Historical Society, as his experience and career progressed, he became a skilled floatplane pilot.

The airplane used in 1929

The plane used in 1929. Source: flyingsanta.org

He would carry mail and supplies to remote communities along the coast. Soon he found himself transporting sick and injured people to safety as well as helping them get medical attention. Wincapaw was a risk-taker, and he would fly when others wouldn’t, as it was typically dangerous to fly through storms and heavy fog. Bad weather didn’t stop him.

Relying on the Lighthouses

Before sophisticated navigational systems were developed, pilots primarily relied on the beams of light from lighthouses in order to navigate New England’s rocky coastline and extreme weather. Wincapaw relied on the lighthouse attendants for their guidance during shaky flights. And they never failed him.

One of the planes flying over the lighthouse

Source: flyingsanta.com

These beacons shined through snow, rain, and all other severe conditions. With time and built-up appreciation for the lighthouse keepers, Wincapaw started to befriend them as well as their families. He valued their steadfast dedication to making sure that the beacons were lit and the waters were safe. After all, his life was in their hands.

A Job of Isolation and Loneliness

In addition to the fact that they helped steer him to safety, Wincapaw also understood that the job of a lighthouse keeper was one of isolation and loneliness. More so, it was the kind of job that is often forgotten. This is precisely why Captain Wincapaw wanted to express his gratitude to the lighthouse community and acknowledge their sacrifices.

Captain Wincapaw dressed as Santa

Source: flyingsanta.org

He just needed to find a way to show it. So, what he decided to do was pack an excess of practical gifts, such as newspapers, tobacco, spices, coffee, candy, soup, and yarn, as well as, of course, small toys for the lighthouse keepers’ children. He stocked his floatplane full and took his first special delivery flight on that Christmas morning.

A Special Delivery

Minutes after takeoff, he used a simple compass for navigation to spot the towering brick construction of the Owl’s Head Light, which sat tall near the entrance of Penobscot Harbor in Rockland. He directed his aircraft to fly within a safe and low distance from the lighthouse and then started dropping a few securely wrapped presents from the plane.

William Jr and Sr dropping packages

William Sr and William Jr Wincapaw. Source: flyingsanta.com

A man dressed in flannel pajamas, a coat, and boots heard the sounds from the plane and rushed out from the keeper’s quarters. Albion Faulkingham waved at Wincapaw as he circled around the lighthouse several times. Faulkingham surely wasn’t expecting to see the Captain flying on Christmas morning of all days. He was also shocked to see presents lying on the frozen ground in front of him.

Becoming an Annual Event

Wincapaw continued to drop gifts at eight more lighthouses in the Rockland area before eventually flying home to spend the rest of the day with his family. To him, it was a nice and deserving mission that he completed. He was unaware, however, that this small gesture would leave a lasting impression.

William Jr and William Sr working inside of the plane while loading it with packages

Source: flyingsanta.org

Just two days later, on a routine flight, Wincapaw spotted the words “Thank You” carefully spelled out with old newspapers on a lawn near one of the lighthouses. His special delivery flight on Christmas Day was so well-received that the Captain decided to make it an annual event, eventually including additional lighthouse posts and Coast Guard stations along the coast of New England.

The Flying Santas

Wincapaw’s son, Bill Jr., an aspiring pilot, took after his father and joined him for the charitable flights. By the time the 1930s rolled around, the father-son duo were dubbed the “Flying Santas” since they started dressing for the part with red velvet suits trimmed with fluffy, white velour under their flight gear.

William and Bill Jr posing at the back of their aircraft with a stack of boxes

William Sr and William Jr Wincapaw. Source: flyingsanta.org

They even attached long white whiskers to their chins. In 1933, the year Bill Jr. earned his pilot’s license, the Wincapaw family moved to Massachusetts. According to William H. Wincapaw III, Bill Jr.’s son, by 1937, the duo was dropping presents for 115 lighthouses and Coast Guard stations in the northeast. The tradition was becoming a full-on program.

A Full-On Program

Eventually, the program became a bit too much for the Wincapaws to manage on their own. Local businesses were kind enough to donate products to help ease the costs, but playing the role of Santa was not just expensive; it was time-consuming. Bill Jr.’s high school history teacher, Edward Rowe Snow, grew to become an essential part of the Flying Santa program.

Edward Rowe Snow working with the other to pack up a plane

Edward Rowe Snow. Source: flyingsanta.com

An author of books on maritime history, Snow was a huge admirer of the Flying Santas. He expressed an interest in helping them out with the program. By 1936, Snow and Bill Jr., who at the time was the youngest licensed pilot in Massachusetts, flew to 25 lighthouses and Coast Guard stations in southern New England.

What Mattered the Most

Meanwhile, Captain Wincapaw took the northern route. After he accepted a job flying mining supplies and gold over the jungles of Bolivia, Wincapaw handed the torch over to his son and Snow for Christmas of 1938. The next year, Wincapaw’s employers flew him back to America in order to fulfill his Flying Santa duties.

Edward Snow delivering packages to two women dressed for a cold winter

Edward Rowe Snow. Source: flyingsanta.com

For the Captain, that particular mission was a 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. The beginning of World War II happened to bring the program to a halt because of wartime obligations and the fear of being hit by enemy aircraft.

A Tragic End

There was, however, one Flying Santa flight that the Army permitted. Army and Navy officials authorized one flight during the conflict in 1941, shortly after the Pearl Harbor attack. And, in order to minimize the risk of the Flying Santas being perceived as an enemy aircraft, they painted the phrase “CHRISTMAS SEAL PLANE” on the Wincapaw plane in two-foot red letters.

William Sr and Jr delivering packages to a group of women

William Sr and Jr Wincapaw. Source: flyingsanta.com

The flights resumed full power after the war ended in 1945. Two years later, on July 16, 1947, Wincapaw suffered a heart attack mid-flight in his Cub Cruiser seaplane on his way out of Rockland Harbor. Sadly, he and the young war veteran on board lost their lives.

RIP William Wincapaw

Wincapaw and the veteran were going for a scenic flight when the plane crashed into the Atlantic Ocean. During the memorial service for the two men, foghorns and lighthouse warning bells rang out in remembrance. But, although Wincapaw Sr. was gone, it didn’t mark the end of the Santa flights.

Anna-Meryle, Dolly, and Edward Rowe Snow posing in Santa-like outfits in 1954

Source: flyingsanta.com

Snow took over Wincapaw’s duties, and the program soared to new heights. Now, with increased support from the Coast Guard, aviation companies, and businesses, Snow flew to lighthouses in Canada and the southern United States, on both the East and West coasts. It even became a family affair, with his wife, Anna-Myrle, and their young daughter, Dolly, joining him for the Christmas-day flights.

It Could Have Been the Driving Santas

In 1981, Snow retired his Santa uniform after 45 years. A non-profit by the name of Friends of Flying Santa, founded in 1997, continued the annual program for Coast Guard personnel and their families. Helicopter companies in New England started donating pilots to help with costs. Brian Tague, the nonprofit’s president, said, “Without the pilots and their helicopters, we’d be the Driving Santas!”

Edward Snow ready to drop a bundle over a lighthouse below him

Edward Rowe Snow about to drop a gift at the Sankaty Head Light in Nantucket 1972. Source: flyingsanta.org

Tague said the Flying Santa obligations include wrapping, labeling, and bagging gifts for over 900 Coast Guard children from 85 different units, flying to 31 locations in six states over four days. A memorial plaque hangs on the wall in a corner at Rockland’s Maine Lighthouse Museum.

“Is That My Flying Santa?”

Seamond Ponsart Roberts first heard about the Flying Santas when she was five years old. In October 1945, her mother told her about the “jolly old fellow” who would deliver dolls to her by airplane. And so for the next three months, whenever Seamond heard an aircraft fly over the lighthouse that they lived in, the little girl would excitedly ask, “Is that him? Is that my Flying Santa?”

Seamond Ponsart with Edward Rowe Snow posing outside of his plane circa the early 1940s

Seamond Ponsart with Edward Rowe Snow circa early 1940s. Source: flyingsanta.org

Her special delivery arrived in the form of a package dropped from a plane that Edward Rowe Snow was flying. Snow’s classic book, Storms and Shipwrecks of New England, was first published in 1943. Through writing and his weekly radio show, he established the legacy of Flying Santa.

Dad Loved It

“Dad loved being Flying Santa,” said Dolly Bicknell, Snow’s daughter who joined him on the flights from her toddler to teen years. “He did it for 40 years and enjoyed dropping presents to the keepers and their families. He and my mother would assemble all the gifts in the basement of our home for weeks leading up to Christmas. He paid for about 90 percent of it.”

Edward Rowe Snow with his wife and daughter standing next to a large pile of packages and dolls

Edward Rowe Snow with his wife and daughter. Source: flyingsantas.org

For Seamond, getting dolls from “her Flying Santa” were the greatest moments of her childhood. She lived a lonely childhood since her family was situated on the remote island of Cuttyhunk, in Buzzards Bay between Rhode Island and Martha’s Vineyard. The tiny island was her playground, as well as her playmate.

The Face of the Flying Santas

With a population of only just a few dozen people, there weren’t many children Seamond’s age. “In 1945, I was a little girl out there with my dogs, cats, and chickens,” Seamond recalled. “I was so excited to be getting a doll from Flying Santa, and I still remember that very special day!” Her father, Octave Ponsart, was the lighthouse keeper.

Edward Rowe Snow dropping a package

Edward Rowe Snow. Source: flyingsanta.com

After Wincapaw died in the plane crash in 1948, and Snow took over, Snow became the face of Flying Santa in newspapers and other media coverage. In 1960, the Associated Press reported that his daughter Dolly, who was only 10 at the time, was excused from school to join her father on the holiday trip in the sky.

Candy Cane Flights

Her English teacher, however, insisted that she write a story about the flight. Snow continued on until his death in 1982. Now, with Friends of Flying Santa, founded by Inga Hanks and Richard Boonisar, Flying Santas still make their deliveries, but they’re mostly “candy cane” flights with ol’ St. Nick distributing the treats to local children.

Edward Rowe and his wife loading packages into the airplane

Edward Rowe Snow and his wife. Source: flyingsantas.org

This year, one of those visits was at Gurnet Light in Plymouth, Massachusetts, the oldest wooden lighthouse in the United States, where more than 50 kids gathered. The chopper landed, and out walked Santa Claus, who listened intently as the excited children shared their Christmas wishes with him.

Razors, Balloons, and Chewing Gum

At its peak in the ‘50s, the Snows delivered coffee, tea, razor blades, rubber balloons, chewing gum, dolls, pen and pencil sets, and more. Snow also ensured that the packages included his latest book. “It was such fun,” Dolly recalled. “Even when I was young, seeing my father dressed as Santa never confused me. I just knew he was acting the part so we could deliver gifts to deserving children and families.”

William Jr and Senior in front of packages

William Jr and William Sr Wincapaw. Source: flyingsanta.org

Tague stated: “Our mission remains dedicated to Captain William Wincapaw and Edward Rowe Snow’s philosophy that lighthouse keepers and Coast Guard crews were true lifesavers and deserved to be recognized for their efforts.” He said that as long as there are boat station crews and other units serving to keep the waters safe, they will do their part to remind them of how much their work is appreciated.

Not all Deliveries Land Alike

Surprisingly, almost all of the gifts remained in good shape despite the fact that they were dropped from a few hundred feet. Snow recorded a better than 90% accuracy rate. Postcards in the packages provided the families with a way to express their gratitude, which also served as a way to gauge the success of the deliveries.

Edward Rowe Snow delivering packages to two women

Edward Rowe Snow. Source: flyingsanta.com

While most of the deliveries were on target and intact, Seamond’s wasn’t one of them in 1945. The doll she had so eagerly waited for broke after the package hit a rock. She cried herself to sleep that night, so her father did his best to repair it. Although in pieces, the doll became especially significant.

Keeping a Promise

“It was my doll, all bandaged up and with her arm in a sling,” Seamond said. “When I played with her the rest of the year, she was my sick doll who had had a very bad accident.” Her mother filled out a postcard and sent it to Snow, and the Flying Santa promised to correct the problem.

People under a lighthouse with rocks spelling out 'Merry Christmas Flying Santas' for the pilots to see

Seasons greetings from the Boston Light 1958. Source: flyingsanta.com

The next Christmas, Snow flew over the Ponsart family residence on Martha’s Vineyard with one of the first commercially available helicopters, and he delivered another doll. “When people ask me about the Flying Santa — and they often do, even now after all these years — my mind instantly turns to a very cold day in my past,” Seamond recalled.

A Personal Delivery

“I am there once again: a little girl in a Red Riding Hood coat at the Gay Head Coast Guard Station, and here comes a helicopter. I had never before even seen a helicopter, and this one is coming right to where we are all standing!”

Snow as Flying Santa with Seamond and her family posing behind a white picket fence

Edward Rowe Snow posing with Seamond and her family 1946. Source: flyingsanta.com

As she watched in wonder, the helicopter landed, and Snow came out of the plane, dressed as Santa. He walked over to the shocked little girl, telling her that he heard about last year’s Christmas present. He then reached into his bag and pulled out the wrapped doll for Seamond. After that moment, the Ponsart and the Snow families became friends. They sent letters to each other every Christmas, and Snow made personal deliveries to whichever lighthouse they were stationed.

The Flying Santa Kid

Seamond and Dolly are still friends today, despite living thousands of miles apart. The little girl with the broken doll retired after a long career in the U.S. Coast Guard. She lives in Louisiana and remains eternally grateful for the generosity of the Santa who wanted to make sure she wasn’t forgotten at Christmas.

Brian Tague, Seamond, and Dolly Snow posing together

Brian Tague, Seamond, and Dolly Snow. Source: flyingsanta.org

“My whole lifelong, I have been and continue to be a Flying Santa kid,” Seamond said. “May they long continue their giving of love from the sky.”

If you’re a fan of true tales from the skies, then the story of Charles Lindbergh, aka the Lone Eagle, is one of the best. That’s next…

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