ROCKLAND — It’s a tradition that began on Dec. 25, 1929, when Capt. William Wincapaw of Friendship loaded his plane with a dozen packages containing newspapers, magazines, coffee, candy and other “island luxuries,” and flew to the lighthouses around the Rockland area and dropped the modest gifts to the lighthouse families living there. According to the history of the Friends of Flying Santa, it was Wincapaw’s way of saying thanks for keeping the lights lit so he could find his way through the skies on foggy, foul-weather days.

Wincapaw was eventually joined on his holiday flights by his son, Bill Jr., and their trips expanded from up and down the Maine coast to Massachusetts, Rhode Island and Connecticut. In 1933, the Wincapaws, who came to be called the Santas by the lighthouse and island families, accepted their roles, grew whiskers and donned red robes. By that year,  they were visiting as many as 91 lighthouses and Coast Guard stations. In 1934, Bill Jr., then-16, was the youngest licensed pilot in Massachusetts.

By then they also had sponsors to help fund the flights and the gift packages. In 1936, the Wincapaw’s enlisted the help of another Mainer, Edward Snow of Winthrop, and the three divvied up the route, with Snow and Bill Jr. flying the southern New England route and Bill Sr. flying the northern route.

When shipping work eventually prevented the Wincapaws from being in Maine for the holidays in the early 1940s, Snow eventually took over aerial Santa duties, accompanied by his wife, Anna Myrtle, with the charter and services of another pilot, Charles Cowan, donated by Wiggins Airways. ”Over the next 60 years, Wiggins would be the provider of a number of ‘sleighs,’ from prop planes to helicopters,” according to the Friends’ history.

During the World War II years, there were some cancellations and delays in the Flying Santa deliveries due to concerns about causing unnecessary air raid alarms, but in 1945 the program was back on track with Snow again making the flights via the Wiggins company. And a year later, the WIncapaws returned from the service and rejoined the Flying Santa effort, with Bill Jr. at the controls and Bill Sr., now 61, along for the ride and the sheer thrill and satisfaction of delivering the packages.

“It took two days of flying to cover the 115 lighthouses and Coast Guard stations from Cohasset, Mass., to the Canadian border. That year, the Wincapaws made sure the flights were completed before Christmas Day, so that for the first time in 18 years, Capt. Wincapaw's wife would have him home on the holiday.”

Less than a year later, in the summer of 1946, tragedy struck: “On July 16, 1947, Capt. Wincapaw, 62, suffered a heart attack shortly after taking off from Rockland Harbor. His Cub Cruiser seaplane nose-dived into the water, and both he and his passenger, 20-year-old Robert Muckenhirn, were killed. On what was supposed to be a pleasant scenic flight over the Rockland area, a young war veteran and an aviation legend were lost. A memorial service was held in Rockland on July 19 that year, and was attended by lighthouse keepers, their families, island residents and representatives of the Coast Guard, Navy and Army. At 2 p.m., 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,” according to the Friends.

With the passing of Bill Sr., Snow stepped in to keep the tradition alive, dropping a memorial wreath in Wincapaw’s honor over Rockalnd Harbor in December 1947, the same year he expanded the program and visited 176 lighthouses and Coast Guard station from Canada to Florida.

“Word came back to him in the days that followed that his gifts of Christmas cheer were extremely well received. The keepers and their families were touched to be remembered on this special holiday. A simple gesture of thanks had made the day so much more special for the residents of these isolated outposts. Wincapaw quickly realized that this Yuletide flight deserved to be repeated as well as expanded to include more of the lighthouse families and Coast Guard stations along the coast,” according to the Friends.

The Flying Santa’s storied history into modern times can be read at the Friends of Flying Santa website, and on Nov. 29, the tradition continued this year for another holiday season.

On Sunday, children of U.S. Coast Guard families up and down the Maine coast were treated to personal visits with the season’s chief elf, Santa Claus, who also had a special gift for each of them inside his giant green and red bags. The jolly elf’s tiny reindeer were given the day off to rest up for the big night coming up, and Santa was ushered this day to Coast Guard communities - from Jonesport to Portsmouth - via helicopter and Friends of Flying Santa.

As the clock inched close to 11:30 a.m., the chopper could be heard in the distance, and then seen as it headed south across the cloudless, bright blue sky and made its way toward Rockland’s Buoy Park on the waterfront. Gathered on the deck of the Maine Lighthouse Museum on Park Street, children and their families stood, peering and pointing as the helicopter touched down, and Santa Claus emerged, waving and “ho ho ho-ing” as he headed to a waiting Rockland Police cruiser.

Making the brief drive up the hill to the front of the Museum, Santa carried two big bags full of toys for the children inside, and settled in a big chair by the Christmas tree. One by one, he read the name on each toy’s tag, placed there by his elves the night before in their workshop, until everybody in the room had their own special gift. For those who wanted to, Santa also invited them to sit on his knee or stand close by and whisper what they wanted for Christmas this year.

And then, just as quick as that, it was time for Santa Claus and his elves, including the pilot and co-pilot of his helicopter “sleigh,” courtesy of heliops.us, to head back up into the sky and continue their visits down the coast. Having already visited children in Jonesport, Southwest Harbor and Castine, Flying Santa’s next stops were Pemaquid Point and Boothbay Harbor, then Portland and Portsmouth, N.H.

Santa had a busy day on Sunday, after which he was due back up to North Pole to check on the elves’ toy making progress and make sure the reindeer - Dasher, Dancer, Prancer, Vixen, Comet, Cupid, Donner and Blitzen - were not only resting but practicing their take-offs and landings to keep limber and in top form. Don’t be surprised if you see Santa back around town though, taking time to listen to children’s wishes in his workshop and appearing in parades and Christmas tree lighting celebrations. He has a way of being everywhere he needs to be this time of year, and they say it’s because he can travel faster than the speed of light. But mostly, it’s best not to ask too many questions - and just believe.

Editorial Director Holly S. Edwards can be reached at hollyedwards@penbaypilot.com or 706-6655.