Kathy McCarthy and her parents greeted Santa at Rockland municipal airport on Monday, December 5, 1960. Edward Rowe Snow was an author and former Navy pilot who became a legend as the North Atlantic Coast's flying Santa. Snow died in 1982. Credit: Spencer Gregory / BDN

Ninety-two years ago, a Maine pilot decided to show his gratitude to the families of hardworking lighthouse keepers in Maine, and bring them some Christmas gifts via float plane.

That simple gesture of goodwill has turned into a nearly century-long tradition that became known as the Flying Santas, a group of volunteer pilots who don the red and white hat and deliver gifts to coastal families and Coast Guard members across New England. They’ve traditionally flown from Washington County all the way to Connecticut — and even, for a few years in the 1950s, to points in California, Florida, the Midwest and Canada.

The program’s roots are in Maine, however, specifically Rockland, where founder William Wincapaw departed from on the first flight in 1929. Today, the Flying Santas are based in Massachusetts, but they still visit a number of sites in Maine every holiday season, including Coast Guard stations in Jonesport, Southwest Harbor, Rockland, Boothbay Harbor and South Portland, all of which the pilots visited on Nov. 28.

The Flying Santas delivered gifts via helicopter to the Coast Guard station in Jonesport, as they have for nearly a century. Credit: Brian Tague / Friends of Flying Santas

Visits to civilian sites in places like Vinalhaven and Pemaquid Point were put on hold due to the pandemic in 2020 and 2021, but Friends of Flying Santas president Brian Tague said the group hopes to bring them back again for 2022.

“Our founder flew during World War II, so we knew we had to do whatever we could to make something happen during the pandemic,” Tague said. “We’ve been doing this for 92 years, and we’d never want to let down these kids and their families.”

A Flying Santa gives a gift to a Coast Guard family in Rockland on Nov. 28. Credit: Brian Tague / Friends of Flying Santas

Pilots initially tossed the packages out of the windows of the planes. According to Tague, the packages, which could weigh up to 25 pounds, occasionally smashed car windows or broke fences, but the organization always paid for any damage.

“These were folks flying in a plane going a minimum of 90 miles per hour,” Tague said. “At some of those off-shore locations, like Ram Island Ledge in Casco Bay, you’d better have had pretty good aim and hope you didn’t smash anything.”

Over the years, packages have included donated products from New England companies, like Gillette razors, La Touraine coffee, Cape Cod potato chips and Bell’s Seasoning. Toys, pens and pencils, candy, toiletries, pet supplies and other goodies have rounded out the packages, though now, the traditional full-family package that’s tossed out of the aircraft is only delivered to the Admiral’s House at Hospital Point Lighthouse in Massachusetts. For the other locations, the organization today focuses on delivering toys on the ground to Coast Guard children.

In the 1940s, flights were scaled back due to World War II, due to concerns about flights causing unnecessary air alarms, or the planes becoming targets for coastal anti-aircraft batteries. For a few years, Flying Santas delivered presents by boat as well.

In July 1947, founder Wincapaw and a passenger were tragically killed in a plane crash off the coast of Rockland, and fellow volunteer Santa Edward Rowe Snow picked up the Flying Santa mantle, organizing annual flights until 1981, the year before his death in 1982. The organization operated through the Hull Lifesaving Museum in Hull, Massachusetts, until 1997, when the Friends of Flying Santas nonprofit was founded.

The means of transport have changed a bit as well. In the late 1970s, faced with increasing costs to operate the flights and new FAA restrictions on where pilots could fly and land, the program began using helicopters instead of planes. Helicopters have been donated by a number of aviation companies and private individuals for more than 20 years, including HeliOps, a Massachusetts-based helicopter company that runs the Maine route.

In the 1980s, the majority of lighthouses began to be automated, resulting in another scaleback in the number of flights, especially in Maine. The organization began to focus primarily on Coast Guard installations, though civilian stops still happen.

Though the organization has changed a lot over the years, the Flying Santas still have a special place in Maine history, including a permanent memorial to founder William Wincapaw at the Maine Lighthouse Museum in Rockland, and as the subject of several children’s books, including “The Flying Santa” by Joe and Paula McHugh, and “Love from the Sky: Seamond and the Flying Santa,” by Angeli Perrow and Heidi Farrow.

“When it started, it was to show appreciation to these folks in these isolated outposts, to make sure they knew someone was thinking about them at Christmas,” Tague said. “Today, it’s really all about the Coast Guard. They’re a small branch of the military, and sometimes they can get overlooked, so we want to tell them we appreciate them.”

Emily Burnham

Emily Burnham is a Maine native and proud Bangorian, covering business, the arts, restaurants and the culture and history of the Bangor region.