New England's Flying Santa

In 1929, aviation was in its infancy. Only two years removed from the Trans-Atlantic flight of Charles Lindbergh, the airplanes of the day were piloted by stout and courageous men.
Navigation in the 1920's was nothing at all like it is today. Not only were there no aids such as GPS, which is the scientific navigational wonder of the modern world, airplanes of the day didn't even have the aid of an installed compass. Forced to fly on only dead reckoning, pilots of the day had to be trained on navigating by landmarks, (night flying was much too dangerous at that time and only the most experienced or foolhearty of pilots would attempt a night flight).
Penobscot Bay is littered with islands, some inhabitable, but a great many were home to the stout people of Maine. With the technology of the 1920's, the quickest way to get from the islands to the mainland was by amphibious plane. We've all seen these aircraft, the kind with the two huge floats under the fusilage which allow the plane to land on the water. A few of the more adventurous spirits around the coast of Maine were making a living transporting people and goods between the islands and mainland.
Enter William Wincapaw.The Friendship, ME native was perhaps the most skilled pilot around these waters. A pioneer in the very early days of aviation, Capt. Wincapaw had honed his trade and was known and respected throughout the region. He was a master pilot of all types of aircraft, but was most at home piloting floatplanes.
In the late 1920's Capt. Wincapaw was directing the operations of the Curtis Flying Service at Rockland's airfield, as well as their operation at a nearby seaplane base. On numerous occasions, he was called upon for emergency transports of the sick and injured on the islands who needed the medical care of the mainland's hospitals. Many times, these transports would occur during storms, or the frequent fogs which would overtake the region. These were, shall we say, less than ideal flying conditions, especially in an aircraft which had no navigational instruments. When landmarks couldn't be seen, Capt. Wincapaw could always count on the dedicated lighthouse keepers, who would always have their beacons shining and foghorns blowing in the worst of what Mother Nature would bring to Maine. By following the lights of the many lighthouses in the region, Capt. Wincapaw would always find his way back to the mainland. The keepers would keep a watch out for his plane, and relay to the next lighthouse that he was coming. They would also relay a message to the airfield, letting them know exactly where his plane was. In that manner, the airfield knew when to expect the plane and would signal the skies around the time it was expected in the area. With every flight he made under those conditions, his appreciation for the keepers and their unfailing dedication to service grew.
In calmer weather, Capt. Wincapaw would often stop at the lighthouses along the bay and chat with the lightkeepers and their families. He got to know their lifestyles better, and realized the sacrifices they made every day. Even the most common necessities of life were often hard to come by, especially for those who served at the more remote lights. Capt. Wincapaw decided it was high time that appreciation was shown to these dedicated keepers.
On Christmas Day, 1929, the captain loaded his plane with about a dozen packages. Included in each package were magazines, coffee, candy, some personal care items and little luxuries to help the families cope with the remoteness of life at these lonely stations. He dropped the packages at lighthouses around the Rockland area, then went home to spend the remainder of Christmas with his family.
In the days to come, word got back to Capt. Wincapaw just how much his small token of kindness and recognition was appreciated by the keepers' families. He realized that this was not only something he needed to do on annual basis, but also an event which needed to be expanded to more lighthouse keepers. The Christmas flights continued every year, and were eventually expanded to keepers along the coast in Massachusetts, Rhode Island, and Connecticut. In order to service all of these keepers, Capt. Wincapaw enlisted the help of his son Bill, Jr., who was to become an accomplished pilot in his own right. When the recipients of the gifts began calling him their "Flying Santa", he began to dress the part, complete with a red suit and whiskers.
By 1933, the Wincapaws had moved to Winthrop, Massachusetts. Their Christmas pages were now accepted at 91 different lighthouses and Coast Guard stations.
As you can imagine, the cost of this program was getting to be quite expensive. The Wincapaws were able to procure a number of sponsors to aid in the cost of not only the packages, but also the planes, themselves. Adriel U. Bird, president of the W.S. Quimby Company of Boston, parent company of La Touraine Coffee, was one of these sponsors. The planes would be painted with the La Touraine name, and the company provided coffee and other financial aid for the packages and flights.
In 1934, Bill Jr., at the age of 16, became the youngest licenced pilot in Massachusetts. That Christmas, he piloted a portion of the route with his father. The following year, Bill, Jr. piloted his own plane for the Christmas runs, enabling the Wincapaws to nearly double the number of lighthouse stations receiving packages.
Around this time, Bill Jr. introduced hi father to one of his high school teachers, Edward Rowe Snow. Snow, a descendant of ship captains always had a keen sense of maritime history. In later life, Snow would author a number of books on lighthouse and maritime history and be considered one of the greatest maritime historians of the twentieth century. The elder Wincapaw knew he needed another capable hand in the Christmas operations, and in Snow, found the perfect man for the job. In 1936, while the elder Wincapaw flew the northern lighthouse route, Snow joined Bill, Jr. on the southern leg.
By 1938, the elder Wincapaw was flying planes in South America and was unable to return to make the Christmas flight. By this time, Snow, (who never learned to pilot a plane), knew the routine and was able to hire a pilot and direct one of the planes, making all of his drops successfully.
In 1940, Bill, Jr. had accompanied his dad in South America and neither could make the Christmas flights. Comfortable in his role of "Flying Santa", Snow was now the master of the Christmas flights, (which now had to take place over a number of days). On one of the flights that year, Snow's wife, Anna-Myrle, played the part of "Mrs. Claus". That would be the first of many flights in which she would accompany her husband. That was also the first year that Wiggins Airways provided a charter plane and pilot Charles Cowan to aid in the drops. Throughout the remainder of the twentieth century, Wiggins provided a number of planes and helicopter "sleighs", as well as pilots, to aid in the Christmas drops.
During WWII, most of the Christmas flights were either cancelled or minimized. In 1945, with the war at an end and the nation getting back to "normalcy", the flights were again being conducted. Our friend Sue Clark, who is a past member of "Friends of Pemaquid Point Lighthouse", recently recounted a story in her blog about a doll dropped at Cuttyhunk Lighthouse that year. You can read about it by clicking here.
The Wincapaws returned in 1946 to help with the Christmas drops. It would be the elder's last.
On July 16, 1947, at the age of 62, Capt. Wincapaw suffered a heart attack while at the controls of his plane. Both he and his 20-year old passenger, Robert Muckenhirn were killed in the crash.
A memorial service was held in Rockland on July 19 and was attended by lighthouse keepers, their families, island residents and representatives of the Coast Guard, Navy and Army. At 2:00, as the service began, fog horns and lighthouse-warning bells rang out across Penobscot Bay in memory of Capt. William H. Wincapaw, the Flying Santa of the lighthouses.
Edward Rowe Snow now was left in charge of the "Flying Santa" program. In 1947, for the first time, packages were dropped along the Atlantic coastline from the Canadian border to the shores of Florida. In all, 176 lighthouses and Coast Guard stations received packages.
In 1953, with the help of a Coast Guard plane, Snow, after starting Christmas Day dropping packages on the East Coast, was able to finish the day with a package drop to stations in Oregon and California on the West Coast. The program, which started as just a way of saying "Thank you" to a dozen lighthouses in Maine, now encompassed more than 200 lighthouses and Coast Guard stations from coast-to-coast!
Eventually, lighthouses on the Great Lakes, Bermuda, and the outreaches of coastal Canada were also added to the Christmas drops.
By the mid-1970's insurance costs and Federal flight regulations almost ended the "Flying Santa" program. By 1977, only Nantucket, Block Island, and Rockland, Maine were on the Christmas package routes.
Frustrated by the restrictions, and with the entire program seriously threatened, Snow searched for a way to rejuvenate the Christmas drops. The answer came to him when he thought back to the aforementioned story in Sue Clark's blog. Although more expensive to charter, helicopters were able to fly without the restrictions of fixed wing aircraft, and wouldn't require the exhorbitant insurace, either. It was a revelation that saved the "Flying Santa" program.
In 1981, Edward Rowe Snow had suffered a stroke and was not expected to be able to make the Christmas drops. Judith Van Hamm, director of the Hull Lifesaving Museum in Massachusetts, just happened to be putting together a tribute to Snow. Upon getting news of his stroke and the impending cancellation of the "Flying Santa" program, She contacted Anna-Myrle Snow, and together they found a way to revive the program. With only a month's preperation time and a very limited budget, Judith Van Hamm was able to procure the help of Wheelabrator-Frye of Maine, a Boston television station and the International Fund for Animal Welfare of Yarmouthport, MA. Raising enough funds for three flights, Ed McCabe, the newly recruited Flying Santa, was able to drop packages at more than 20 stations from West Quoddy Maine to Warwick, RI.
On April 12, 1982, Edward Rowe Snow passed away at the age of 79.
The Hull Lifesaving Museum was now the keeper of the program. In 1982, George Morgan, who saw an article on the efforts of the museum to keep the program alive, joined Ed McCabe as a "Flying Santa". Ed would take the northern route, while George would direct the southern route. Eventually, George Morgan, with an assist from his wife Jean, would become director of the museum's "Flying Santa" program. By 1987, due to the automation of nearly all of Maine's lighthouses, the northern leg of the trip was cancelled. Only 15 southern New England lighthouses were visited by George that year.
With the automation of every lighthouse in the country except Boston Harbor Light, it appeared as if the "Flying Santa" program was dead. Only a ceremonious drop at Boston Light was keeping the program alive.
With the advent of lighthouses being handed over to non-profits, and some lighthouses, although automated, remaining manned by Coast Guard personnel, the program slowly expanded once again. By 1997, having outgrown the museum's capabilities, the program was taken over by a newly-formed volunteer group called "Friends of Flying Santa". Many of the group's members are involved with other lighthouse organizations, making their tie to this program a personal one.
Today, under the direction of this group, the "Flying Santa" program is alive and well. Although the role of Santa has been filled by a number of different individuals in recent years, the program still sticks to its roots, delivering packages to many of the lighthouses first visited by William Wincapaw in his intial "thank you" flight!
(*Thanks to the "Friends of Fling Santa" and their website, which contributed much of the history for this article.)