William H. Wincapaw…The Flying Santa Claus

Wed, Dec 13, 2023 at 5:27PM

The original Flying Santa Captain William Wincapaw

You know Dasher and Dancer, and Prancer and Vixen, Comet and Cupid, and Donner and Blitzen. But do you recall William Wincapaw, the most famous New England Lighthouse Santa’s helper of all?

The sea that beats against Maine’s rocky coast is an unforgiving and demanding mistress. The frigid, violent, and wholly unpredictable nature of this remote corner of the North Atlantic tempers the mind and body of any who work upon it. Like a cold, wet anvil of ice, this unforgiving environment forges a particularly rare breed of men and women who are known for their fortitude, independent nature, and pragmatic attitude.

Like most New England fishermen, Wincapaw possessed a strong work ethic and heightened sense of responsibility. He believed in the importance of family and friends, aiding those in distress, and showing appreciation for help when help was given. In addition to learning these important values, William also grew to understand the unpredictable nature of the sea and how survival often depended on one’s ability to remain focused and solve problems. These life experiences, coupled with a strong moral upbringing produced a young man of exceptional character.

William H. Wincapaw loved adventure and was fascinated by all things mechanical including automobiles, boats, and bicycles. When news of Wright Brothers successful flight at Kitty Hawk, NC, swept the nation in 1903, the 18-year-old tinkerer daredevil was immediately bitten by the aviation bug. Earning a mechanical engineering degree from the Pratt Institute in 1910, Wincapaw pursued his dream of becoming a pilot by enrolling in the Curtiss Flying School in 1911. He earned his wings a few months later after completing his first solo flight.

True to his New England upbringing, Wincapaw wasted little time getting a commercial air delivery business off the ground. Operating out of Rockland, Maine, the young aviator spent the next six years ferrying people and supplies up and down the New England coast before helping the Army Air Service train combat pilots during WWI. Capitalizing on the public’s post-war fascination with aerial combat maneuvers and acrobatics, Wincapaw worked the barnstorming circuit for several years, amazing crowds of spectators with his exceptional flying skills at fairs, air shows, and festivals across the country.

Returning to his home state of Maine in 1924, William Wincapaw became president and general manager of Richmond Airways, an air delivery service he would run until 1926. Joining the Curtiss-Wright Flying Service at the bequest of Glenn Curtiss himself, Wincapaw spent the next five years selecting, building, and managing airports and seaplane facilities throughout New England while still serving as one of the company’s chief pilots.

In addition to being a highly respected aviator, Wincapaw was also a well-known humanitarian who had rescued numerous mariners in distress throughout his career. Having grown up in the small town of Friendship, Wincapaw understood how much reliable air service meant to the residents of Maine’s coastal communities. Not only did his timely arrivals help them feel less isolated from the outside world, but his ability to provide emergency transportation to the sick and injured was often a matter of life and death. Unwilling to let these people down, the veteran pilot would take his float plane aloft in weather that left most others tethered firmly to the ground.

Although possessing a level of skill on par with America’s most renowned early aviators, Wincapaw’s true claim to fame stemmed less from what he could do with an airplane and more with the lighthouse tradition he started with it.

Before the development of sophisticated electronic systems, aviators relied solely on a magnetic compass, a map, and landmarks to get from one place to another. Although designed for maritime navigation purposes, lighthouses (and Fresnel lenses in particular) proved so effective in aiding aeronautical navigation that the US Lighthouse Service had its own airways division from 1926 until 1933. Standing out from the surrounding countryside and illuminated by a bright shining beacon, lighthouses were easy to recognize from the air. This visibility, coupled with the clear identification of beacons on navigational charts, made lighthouses important reference points for coastal pilots.

Recognizing that the families living on remote light stations were often starved for social interaction, Wincapaw made it a point to visit them whenever possible. One can only imagine the excitement the lighthouse keeper and his family felt whenever “Captain Bill” was spotted overhead, or the flurry of activity that ensued when the pontoons of his float plane touched down just offshore. Whether stopping by to deliver packages or simply to sit and chat for a spell, William’s arrival was always a happy and welcome event. This simple act of kindness was indicative of his exceptional character and one of the many reasons he was so highly regarded by those who knew him.

Lighthouses had always held a special place in Bill’s heart. However, the depth of appreciation he felt for them and those who manned them stemmed from much more than their simple use as landmarks. In 1929 they saved his life.

The morning of December 21, 1929, felt like a typical winter day in Maine when William Wincapaw loaded his Travel Air A-6000A (later known as the Curtiss-Wright 6B) floatplane with packages bound for several coastal communities. Although the wind had started to pick up by the time he was aloft, it was nothing the veteran flier hadn’t flown through before. Besides, it was almost December 25th and Bill was sure several of his parcels were destined for placement under yuletide trees. Unwilling to be responsible for breaking a child’s heart on Christmas morning, William pushed on. In his mind, neither rain nor snow, nor sleet nor dark of night would keep him from making his appointed rounds.

The Travel Air A-6000A (later known as the Curtiss-Wright 6B) floatplane that William Wincapaw flew in 1929.
The Travel Air A-6000A (later known as the Curtiss-Wright 6B) floatplane that William Wincapaw flew in 1929.

Landing and taking off several times, Bill delivered packages along his intended route as the weather continued to deteriorate around him. By mid-afternoon, dark clouds laden with heavy snow had moved in overhead. Hoping to complete his deliveries before the storm hit, Wincapaw continued flying south until he realized he had simply run out of time.
Blinded by thick falling snow and buffeted by intense wind gusts that threatened to tear the canvas from his wings, William had just decided to turn back when he discovered his compass had stopped working. Searching for a visible landmark to steer by, he could only watch in dismay as the intensity of the strengthening storm reduced his visibility to zero.
Never had he experienced snow or winds of this magnitude. Blinded by the near blizzard conditions and disoriented without the aid of a functioning compass, Captain William H. Wincapaw knew he was in serious trouble. Was he headed inland or out to sea? Was he traveling north or south? There was simply no way to know for sure. Desperate to find anything that could help him steer his plane in the right direction, William continued to stare out the cockpit window. If an opportunity did not present itself soon, he would have to attempt a crash landing and simply hope for the best.
Running dangerously low on fuel, Wincapaw was nearing despair when he spotted a flicker of light through the windscreen. Turning the aircraft towards this faint glimmer of hope, his spirits soared as the dim light steadily grew into the intense beam of a lighthouse beacon. Circling the tower, Bill quickly recognized the short white lighthouse with attached keeper’s dwelling as the Dice Head Lighthouse at the head of Penobscot Bay! He had overflown his destination by nearly 20 miles but knowing this section of Maine’s coastline like the back of his hand, he simply flew south from one lighthouse to another until he reached Rockport Bay safe and sound.

The Dice Head Lighthouse which marks the east entrance to Penobscot Bay saved Captain Bill’s life on December 21, 1929.
The Dice Head Lighthouse which marks the east entrance to Penobscot Bay saved Captain Bill’s life on December 21, 1929.

Reunited with his family once again, Captain Wincapaw reflected on the dedication of the lighthouse keepers who maintained the lights that had helped guide him home. He knew many of these men and women personally and deeply appreciated the sacrifices they made in the performance of their assigned duties. Although he owed them a debt of gratitude that he could never fully repay, Captain Bill was determined to try and knew just how to do it. Taking a page from the handbook of the Jolly Old Elf himself, William Wincapaw would express his thanks by spreading Christmas cheer at lighthouses up and down the coast of Maine!
With the help of his wife and children, Captain Bill spent the next few days assembling dozens of care packages that were later loaded aboard his float plane. Intended for the lighthouse keepers and their families, the holiday bundles contained a wide assortment of items including tea, candy, coffee, magazines, and other common staples that would have been considered luxuries by those living on the remote light stations.
William Wincapaw lifted off from Rockport Bay on the morning of December 25, 1929 to deliver his gifts. Like a modern-day St. Nick with a sleigh pulled by a nine-cylinder Pratt & Whitney radial engine rather than 9 overfed reindeer, the “Flying Santa Claus” flew along the coast dropping his packages of Christmas cheer to lighthouses below. One can only imagine the look of confusion that must have appeared in the eyes of the keepers and their families when his plane flew by overhead and the feeling of joy that they must have felt when the bundles filled with goodies landed at their feet.
The level of appreciation expressed by the lighthouse keepers and their families was tremendous. Amazed by the response, William decided that his Christmas deliveries should not only be repeated the following year but expanded to include even more lighthouses. In 1933, Captain Bill’s holiday delivery route included 91 lighthouses from Maine to Connecticut. By 1940 that number had increased to more than 150 light stations and Coast Guard facilities. What had originally begun in 1929 as a single pilot’s gesture of goodwill had grown into a holiday tradition that spanned the entire New England coastline.
In 1935, Wincapaw’s 16-year-old son Bill Jr. joined the Flying Santa flight team. Although he had accompanied his father on numerous Christmas deliveries in the past, the newly licensed pilot had never flown a route on his own. The apple must not have fallen far from the tree however because the younger pilot performed admirably and later grew into a well-respected and accomplished pilot in his own right. Bill Jr. would continue to serve as a Flying Santa until 1946. In 1936, William Wincapaw asked Bill Jr.’s high school teacher Edward Rowe Snow to help organize and promote the Flying Santa program and accompany Bill Jr. on his Christmas flights. Snow greatly admired what the Wincapaw family was doing and jumped at the opportunity to contribute to the worthy cause. Although he was not a pilot, his enthusiasm, wit, and engaging personality helped secure the support of many regional corporations including the La Touraine Coffee Company, Brickford’s Restaurants, and Wiggins Airways. Originally paid for entirely out of Wincapaw’s own pocket, this invaluable sponsorship helped ensure the program’s continued success and growth in the decades to come.

Captain William Wincapaw and son Bill Jr. delivering presents in 1946
Captain William Wincapaw and son Bill Jr. delivering presents in 1946

Despite business and wartime obligations that sometimes prevented him from making his Christmas deliveries in the early 1940s, Captain Bill remained committed to the beloved holiday tradition he had founded until dying from a heart attack in 1947. Although gone, the original Flying Santa’s memory lived on in the hearts and minds of all who knew him. When asked to describe the impact of Wincapaw’s legacy, Ed Snow responded, “Bill had a heart as big as anyone I have ever known. His thoughtfulness in beginning the lighthouse flights will never be forgotten by the lighthouse keepers and Coast Guardsmen up and down the New England coast.” On December 25, 1947, Snow dropped a wreath over Rockland Harbor in honor of his long-time friend and mentor.
Assuming the mantle of leadership following William Wincapaw’s death, Snow’s dedication to the Flying Santa program rivaled that of its founder. In 1947, Snow expanded the flights to include 176 lighthouses and Coast Guard stations from Canada to Florida. By 1953, packages containing a wide variety of donated products ranging from coffee, tea, and razor blades to candy, toys, and school supplies were being dropped at lighthouses along both coasts and within the Caribbean. Under Snow’s leadership, the cherished New England holiday tradition begun by Captain Bill in 1929 had become a nationwide event.

Flying Santa over Boston Light in 1947
Flying Santa over Boston Light in 1947

Edward Rowe Snow remained active in the Flying Santa program for more than forty years. What makes his accomplishments even more remarkable was the fact that he never learned how to fly a plane. Every one of his annual yuletide deliveries was made in a chartered plane that he often paid for himself. Although it was an expense he and his wife could ill afford, the Snow family felt the benefits of the Flying Santa program were well worth the financial cost and personal sacrifices that they made to pay for it.

Edward Rowe Snow and his wife Anna load an airplane full of Christmas packages for their annual Flying Santa trip in 1963
Edward Rowe Snow and his wife Anna load an airplane full of Christmas packages for their annual Flying Santa trip in 1963

In 1981, Snow suffered a stroke that prevented him from making any future deliveries as the Flying Santa Claus. Hearing that New England’s lighthouse families would not be visited by the Flying Santa for the first time since 1942, Judeth Van Hamm, director of the Hull Lifesaving Museum, offered the Snow family her assistance. Securing the volunteer services of pilot Ed McCabe and support of regional businesses, Ms. Van Hamm organized that year’s flight with McCabe, dressed in Edward Snow’s red Santa suit, at the controls.
Edward Rowe Snow passed away at the age of 79 on April 12, 1982. The author of more than 90 books as well as being a highly respected teacher, historian, lecturer, radio personality, photographer, and World War II veteran, Mr. Snow will always be remembered for his generosity, caring spirit, and dedication to spreading Christmas cheer.

Coast Guard residents at Boston Light send a cheerful season’s greetings to Ed Snow the “Flying Santa” in 1958.
Coast Guard residents at Boston Light send a cheerful season’s greetings to Ed Snow the “Flying Santa” in 1958.

Although William Wincapaw and Edward Snow are gone from this world, their legacy will live on in the hearts, minds, and actions of every pilot who takes to the sky dressed as Santa Claus, now and in the years to come.

Although William Wincapaw and Ed Snow are gone, the Flying Santa tradition lives on.
Although William Wincapaw and Ed Snow are gone, the Flying Santa tradition lives on.

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