The History of flying Santa

By Shelley Wigglesworth

Santa Claus doesn’t always travel by sleigh and reindeer. He has also been known to take a helicopter to special destinations, and one of those special locations is the Trust’s own Goat Island Lighthouse. What started out as an act of goodwill to Lighthouse Keepers in Rockland, Maine at Christmastime in 1929 has become a time honored, symbolic holiday tradition that presently includes thirty lighthouse stations along the New England coast and islands. Traditionally, packages were dropped from the sky, bringing necessities from the mainland along with gifts for the lighthouse keepers and their families for the holidays. These days, Santa is escorted by a pilot, and when weather conditions allow, the helicopter lands for a quick personal visit to islanders and visitors to deliver gifts.

Goat Island Lighthouse in Cape Porpoise, which is maintained by the Kennebunkport Conservation Trust is one of the original Flying Santa drop off locations. Tom Bradbury, Executive Director of the Kennebunkport Conservation Trust said:

We look forward each year to the time-honored tradition of the Flying Santa. It reminds us of the many who have served Goat Island, and other light stations, over the years, the sacrifices those families made, the difficulties they faced and the significant role they played in protecting our coastline and harbors.  It also taught us that no matter how old we get, we feel like children again when the sound of the helicopter is heard approaching the island and Santa comes into view. It never grows old.  

Goat Island Lighthouse keeper Scott Dombrowski lives on the island for most of the year with his wife Karen. He added “We’re honored to be the lighthouse keepers at Goat Island for the Kennebunkport Conservation Trust and keeping such time-honored lighthouse traditions alive. Sharing the Flying Santa stories, or for a lucky few each year, the full experience, is incredibly special for us to pass along.” He elaborated “Flying Santa is an amazing experience. Our children grew up on Goat Island and their anticipation and excitement at Christmastime watching, waiting for, hearing, then seeing Santa on the horizon getting closer and closer, circling overhead in the helicopter and then the sudden rush of goosebumps we all experienced when seeing Santa waving at eye level as the helicopter lowered below will always be a magical memory for us.”

The Flying Santa concept is the brainchild of Maine floatplane pilot Captain William Wincapaw. Wincapaw recognized and appreciated the diligent work and sacrifices of the lighthouse keepers and their families to keep mariner’s safe early on. In the early 1920’s he began flying his own small aircraft over Maine islands to drop off supplies to lighthouse keepers and their families. As a result, he was also called in to air lift passengers during emergencies and when travel by boat to the mainland was dangerous. Wincapaw is credited with saving the lives of dozens of men, women, and children over the years.

Just as those on the islands depended on the assistance of transportation by aircraft, Wincapaw also depended on the light and sound from the foghorn to navigate the many dangerous emergency trips he made during inclement weather, and by night. On some occasions, the audio and visual cues provided by area lighthouses were the only means for the pilot to navigate the coastline and reach those in need with supplies and assistance. This interdependent relationship resulted in not only a beneficial partnership, but a special bond between Wincapaw and the people of the islands, prompting Wincapaw to make a heartfelt, secret, and special delivery on Christmas day 92 years ago. The yearly event continues as a symbolic gesture nearly a century later.

Here is how it all began. In the early morning hours of December 25, 1929, Wincapaw loaded his plane with previously prepared and bundled packages of supplies, gifts, trinkets, candy, and toys for island families, considering the individual family members and their interests. He then flew over the lighthouses in the vicinity and air dropped these bundles, much to the delight and surprise of islanders. The islanders, who were so isolated from the conveniences of the mainland and day to day bustle of the outside world were not only appreciative, but also deeply touched by the gesture.

Because of this, Wincapaw decided to make the Flying Santa Christmas drop a yearly tradition, and with the help of other pilots, he eventually expanded his route to cover lighthouses up and down the coast of New England with drop off locations in Maine alone totaling 117 at one point.

Today, with the help of donors, volunteer Santa’s, and pilots from all over New England, the Flying Santa tradition, which is steeped in good memories and good will, lives on, along with the spirit of Captain William Wincapaw and the true meaning of Christmas.

*Note: Because of Covid, only a handful of flights have taken place in recent years. *

For more information on Flying Santa and upcoming Flying Santa lighthouse drops and visits throughout New England please visit: http://www.flyingsanta.com/  or email info@flyingsanta.org