CLIFF ISLAND — They knew they’d have to ambush Chester Pettengill if they wanted to make a fuss over his 80th birthday.

The beloved lifelong islander has a reputation for being humble and shy as much as he’s known for being a dependable and indispensable neighbor, friend and caretaker.

About 40 islanders of all ages converged on the ferry dock late Saturday morning, when they knew Pettengill would be there to meet the 11:35 mail run from Portland. Bundled in hats and scarves against a brisk winter wind, they encircled the baffled-looking man.

“What did I do?” Pettengill asked, displaying his characteristic dry wit.

What Pettengill has done over the last several decades is carry on traditions of caring and community service that long went unlabeled in a place where those habits are necessary to survive the harsher aspects of life on Casco Bay.

Pettengill is best known as the island’s one-man welcome wagon, meeting almost every ferry – three to five a day – that makes the two-hour trip from Portland. He lugs mail to and from the post office, something he has done for 29 years, and he offers rides and delivers packages to islanders in his black Nissan Pathfinder. And for 60 years he has been custodian of the small school that today serves a handful of children who live on the island year-round.

Portland City Councilor Belinda Ray read a proclamation on the ferry dock that described Pettengill as the island caregiver, unofficial taxi driver, historian, musician and artist, among other attributes.

“He is a guardian angel who watches over everyone’s homes, families and beautiful Cliff Island,” Ray said. “Chester has a twinkle in his eye and a smile in his heart and is a dear friend to all.”

Pettengill shook his head in mock disagreement with the twinkle reference.


Pettengill’s great-great-grandfather Samuel, an Englishman, settled the island in 1813. He owned about half of the 2-mile-long island and farmed a good part of it. Two generations later, when Pettengill’s grandfather married a member of the Griffin family, which owned the rest of the island, Pettengills pretty much owned the whole thing.

Pettengill’s grandfather was custodian of the island school from the time it was built in the 1890s until Pettengill’s father took over in 1907. His mother assumed the job in 1936 when his father died, and Pettengill started helping her in 1955, shortly after he graduated from Portland High School.

When he was a young man, Pettengill worked as a sternman on a lobster boat for about 20 years. He also read electric meters on the island for about 20 years. The youngest of three children, Pettengill never married or had children of his own.

“After my brother and sister left the island, I stayed and took care of my mother for years,” Pettengill said. “I always felt I belonged here. I would have been more involved with music otherwise, but you have to make choices.”

Islanders say Pettengill is a concert-worthy pianist, a talent he picked up from an island resident as a child and honed by taking lessons on the mainland during high school. He still plays at school events and at the island church, a Seventh-day Adventist congregation.

“He’s really on a professional level, but he won’t tell you that,” said Anna Dyer, 69, another lifelong island resident who was postmaster for many years.

“Chester is the spirit of Cliff Island,” Dyer said. “He’s humble and unassuming. He does what he needs to do, he helps people and he does it quietly.”

Pettengill is also a painter and photographer. He takes photos of the island every day and posts them on Facebook to promote the beauty of the place, Dyer said.

“He doesn’t take a day off,” Dyer said. “He goes out in all kinds of weather.”


There are about six lifelong residents left on the island, where the year-round population of about 50 people swells to as many as 300 in the summer. Several seasonal and former residents made a point of attending Saturday’s party for Pettengill, which continued at the island store, where they shared a birthday cake.

“Chester always had my back,” said Nancylou Stiles of Standish, 73, who raised four children on the island as a single mom. “He carried groceries. Kept an eye on things. He’d check my house when I was gone and he’d tell me later that he had shut my stove off.”

During the gathering, Nick Mavodones, a city councilor and operations manager of Casco Bay Lines, gave Pettengill a shiny brass nautical bell to show appreciation “for everything you’ve done, not only for the Bay Lines, but for everyone here.”

It all seemed to be a bit much for Pettengill – the bell, the proclamation, the cake and all those people singing two rounds of “Happy Birthday,” first on the dock and then in the island store. His sister Louise, who moved back to the island recently, had told him they were meeting one person at the ferry dock.

“I was shocked,” Pettengill said later, as the islanders headed back to their homes. “I didn’t realize there was going to be a multitude of people. I’m not used to being the focus of a crowd. But it was nice.”


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