Recalling a Flying Santa Visit to Fort Point Light

By Bob Trapani, Jr. December 6, 2021

For over nine decades, the beloved Flying Santa made a number of visits to Fort Point Lighthouse in Stockton Springs during his annual Christmastime journey through the skies of Maine.

Whether it was for the keeper and his family during the days when the lighthouse was staffed, or later when parents and children from the local community gathered together, the tradition of Flying Santa has burned bright at Fort Point Light.

Why and how you might ask?

Well, as history points out, lighthouses have long held a special place in the heart of the Flying Santa. His mission was born out of a desire to show appreciation for the keepers and their families who faithfully tended the lights.

According to the New England Historical Society’s website, “Bill Wincapaw was a skilled floatplane pilot who flew mail, medicine and supplies to remote coastal communities. He also flew sick and injured people to safety or to get medical help, often in bad weather. It was a dangerous job. In those days, pilots flew by dead reckoning or with rudimentary navigational aids and landmarks. Radar hadn’t been invented yet, and airplanes had no radios.

“In 1929, Wincapaw got lost in a winter storm over the North Atlantic. His compass failed, and his plane was dangerously low on fuel. Finally, to his relief, he spotted the beam of a lighthouse – and then another. He followed the beacons to a safe landing. That wasn’t the only time lighthouse beacons saved Wincapaw’s life in a storm. The lighthouse keepers looked out for him through the year, and relayed back to the airfield when he safely passed their stations.”

The Flying Santa, which started in 1929, originally used an airplane to bring joy and gift bundles to those stationed at lighthouses. His plane would swoop in low over the lights as he dropped Christmas packages to eager recipients below, but by the 1980s, his aircraft of choice became the helicopter. The helicopter provided Flying Santa with an opportunity to land and make personal deliveries of gifts to children gathered at each of the U.S. Coast Guard stations and lighthouses on his list.

When the Flying Santa flights originated, they were carried out on Christmas Day. But as the flights expanded to more lighthouses, and then well beyond the boundaries of Maine, these annual visits occurred anywhere between one and four weeks before Christmas.

I personally had the privilege to witness firsthand a Flying Santa visit to Fort Point Lighthouse on December 18, 2010. What a joy it was! Watching Flying Santa arrive at Fort Point was nothing short of pure wonderment! The station looked amazing with festive decorations adorning the buildings and grounds and the light’s fourth order Fresnel lens was vigilantly ablaze. Even a blanket of snow covered the grass, which served as a sort of “welcome mat” for Flying Santa. The stage was perfectly set for a winter wonderland moment with a Christmas touch.

As one might expect, the excitement for the arrival of Flying Santa started to build well in advance of his helicopter touching down at Fort Point Lighthouse. Even before those who had gathered could catch a glimpse of the flying craft with their eyes, they were focused on the moment at hand with their ears – waiting to hear the helicopter’s rotors reverberating through the frigid air.

Suddenly, a child exclaimed, “I think I hear it – I think I hear it!”

The exuberance of the alert instantly banished all feelings of youthful impatience. Another child followed, saying, “I see it – there’s Santa!” Yet another voice said, “Where, I can’t see him?” An excited comeback exclaimed, “Right there, don’t you see that black dot?”

Seconds later, all could see the fascinating sight of Flying Santa’s helicopter growing larger in the sky as it approached. When it arrived at the lighthouse, the helicopter hovered above the ground for a few moments before landing. While doing so, the helicopter caused a rotor wash of snow that instantly created a magical grand entrance for Flying Santa. For when the snow settled, out stepped the Jolly Fella to the delight of all.

There to greet Santa as he strolled over to the lighthouse was Terry and Jeri Cole who resided at the historic site and had gone to great lengths to ensure this wonderful Maine tradition was met with a fine showing at Fort Point Light.

“Since the return of Flying Santa to Fort Point Light Station in 1996, it evolved into a very fun and rewarding event,” said Terry Cole, Park Ranger for Maine Bureau of Parks and Land (Terry retired from this position in 2021). “Besides our family and neighbors, we would invite a number of children from the local schools. These were kids who could benefit from something special in their lives at Christmas. A parent once told me that Flying Santa ‘was something they will remember all their lives.’ Hearing something like this was so great, for the goals of the Park are to educate and make the lighthouse more accessible – and the annual Flying Santa event certainly helped to achieve these goals.”

Cole went on to say, “For my family, Fort Point Light was our first real home together. I was extremely fortunate to be with my family all the time here at the lighthouse – first as a Coast Guard keeper from 1973-76, and later as a park ranger at the site starting in 1988. For so many of us, Christmas is a time of togetherness and warmth, and at Fort Point Light Station, there was something charming and magical about the place that added to these feelings.”

The Flying Santa experience extended the spirit of Christmas that “keeper” Cole alludes to with others, but not without the help of a dedicated and talented hand. As her husband pointed out, Jeri Cole made all the difference. “Jeri did an awesome job at pulling this event together over the years,” said Terry Cole. “She coordinated with Flying Santa, and with the families who attended, decorated the house and baked cookies, which everyone enjoyed over a cup of hot chocolate after Santa left.”

With greens, red ribbons and ornamental candy canes accenting the light station grounds, Flying Santa sat down in his special chair to greet the children on this memorable day in 2010. The heartwarming scene not only exuded the spirit of Christmas, but also the grandeur of lighthouses. During special moments like this, the benevolent blend could not have shone brighter!

Calling the names of the children one by one, Santa not only presented the children with a wrapped gift, he also shared with them unbridled joy.

It was not important whether the children fully understood the magnitude of this heartwarming tradition in the moment, for the Flying Santa experience is an enduring one that only grows sweeter with the passage of time.

When referring to his daughters Melissa and Amanda, Terry Cole noted, “My daughters were always a big help in the past and I expect that the grand kids will be more involved with preparation and assisting Santa in the future. The Flying Santa event has been a reminder of all our happy times here as a family – both when our girls were young and later when we got a second chance watching our grandchildren in a similar but entirely new way.”

Maybe Flying Santa’s greatest gift of all is not one that can measured by material, but rather only by the wonderful joy this Christmas tradition has fashioned in the hearts and minds of those who have been blessed to be a part of it. Merry Christmas!

To learn more about the Flying Santa, visit the Friends of Flying Santa’s website: www.flyingsanta.org