LITTLETON — The community is mourning the loss of Gerald Winn, New Hampshire’s longest consecutively serving town moderator who dedicated himself in service to his community and provided a guiding hand for more than half a century.

Winn died Sunday morning after a battle with cancer. He was 84.

He is survived by his wife of 62 years, Mona, sons Greg Winn and Jeff Winn, daughter Carrie Gendreau, and eight grandchildren.

“Even though we knew it was coming, it’s still a tough thing,” Gendreau said Tuesday.

Before Monday’s Board of Selectmen’s meeting, board vice-chairman Roger Emerson called for a moment of silence.

Upon learning of Winn’s passing, scores of people in the community reached out to his family.

“The condolences and outpouring of support have been amazing,” said Gendreau.

In September, Winn retired as Littleton’s town moderator, after serving for 56 years.

In November, he was named 2021 Littleton Citizen of the Year by the Littleton Area Chamber of Commerce, which honored Winn for “outstanding citizenship,” for bringing an “exemplary vision, pride, and commitment to the betterment of society,” and for giving tirelessly to his community for decades.

In the same ceremony, Winn was honored with proclamations by the New Hampshire Senate, which recognized his “devoted service as Littleton town moderator,” and by Gov. Chris Sununu, who recognized Winn for his decades of leadership and the “knowledge, patience and accessibility that he brought to each of his roles.”

On Tuesday, Janet Parker, owner of Littleton Office Supply, called Winn a born leader and said the community lost someone who was constantly giving.

“He always had a helping hand for anybody and everyone, from a business and personal standpoint,” she said.

Parker called Winn a good person who was always quick with a laugh and was one of the true founders of the town as it entered its modern era.

“He gave so much to the town of Littleton for so many years,” she said.

In 1959, Winn, a native of Piermont, moved to Littleton, where he took the automotive and mechanic skills he learned in the Air National Guard and opened up Winn’s Flying A service station.

In 1965, after taking a Dale Carnegie course on public speaking (and eventually becoming a Dale Carnegie instructor), Winn ran for Littleton town moderator and was first elected in 1966, at the age of 28.

After running his gas station for several years, he and Mona ventured into the real estate business and together built Century 21 Winn Associates.

In service to the town, Winn would also serve on the Littleton School Board and would serve as a community leader in many capacities.

In 1996, with his moderator skills in demand, he was elected school district moderator.

“Dad knew that people really liked and appreciated him, and he knew or hoped that he had made an impact on people,” said Gendreau. “With Dale Carnegie, the garage, his real estate, his church, his life with the town and the school, his fingerprints were on everyone. Many people would say they were in his real estate class, or in his adult Sunday School class, or he was helpful in getting them a home when they came to town, and he welcomed them.”

Chad Stearns, a community relationship banker with Mascoma Savings Bank and a former Littleton selectman, was born in the era when Winn was already town moderator, but came to know Winn when he, Stearns, was becoming executive director of the chamber of commerce.

“The first interview I had was in the basement of Century 21,” said Stearns. “I really got to know him well through a lot of chamber work, but he was also a Dale Carnegie instructor, and I feel that class, that training, really helped me get over my fear of public speaking and public engagement. He had a great impact on me. Through those courses, I was really able to come out of my shell and become a community leader. It got me to be able to take that leap out of my comfort zone.”

Stearns reflected on Winn’s community impact.

“I think he had a calming voice for town meetings,” said Stearns. “He was really was able to bring all kinds of different ideas under one roof, under one meeting, in an orderly fashion. He was always a cheerful face when you would go to vote at the polls, regardless of what election it was or what you were voting on. He was always a knowledgeable, friendly face. He set the bar very high for running town meetings and elections.”

Steve Kelley, a longtime member of the town-school budget committee and chairman of the committee for more than two decades, met Winn nearly 50 years ago, in 1974, when Kelley moved from his native Berlin to make Littleton his home.

“Gerald embodied what it meant to be a corporate citizen of Littleton, somebody who was willing and able to give above and beyond for the good of the community,” said Kelley. “He was the kind of person who, in time, people would turn to more and more often for answers or direction. Gerald in many ways had figured it out.”

Kelley recalled some town meetings where tempers would rise on some issues being debated.

“Gerald had a great deal of natural talent for smoothing over situations, for getting people to interact in a civil and productive fashion,” said Kelley. “He could ask the question that could cause parties on both sides of an issue to think a little deeper and probably realize that they weren’t as far apart as they had thought and that they deserve to show each other respect … If he had a number one talent, it was for lowering the temperature of a situation and bringing the boiling pot down to a simmer to make for a more productive conversation. Whoever follows in his shoes is going to have big shoes to fill.”

While many residents remember Winn as the man in a suit and tie behind the podium moderating town and school meetings, Gendreau said there is another side to her father — a man just as comfortable outdoors in jeans and a flannel shirt working on his land.

“It’s such a different side of dad, but the side that he really loved,” said Gendreau.

For nearly 25 years, Winn and Mona owned 200 acres in Littleton near the Dalton town line.

“Dad would do the mowing in the fields,” said Gendreau. “They created trails, so mom and dad would go four-wheeling. They have cameras all over so they can watch wildlife. They just love spending time on the land.”

When he first become town moderator, Winn, during his Citizen of the Year honors in November, said he didn’t expect to serve for the long haul.

He said his objective as moderator was to give everyone a full opportunity to speak and never leave the meeting feeling that they were denied that opportunity.

“It’s the people’s meeting,” said Winn.

Because of the high numbers of COVID-19 cases, a celebration of Winn’s life is scheduled later this spring, at 11 a.m. May 14 at Monroe Village Cemetery, followed by a reception at Monroe Town Hall.

“It was a difficult decision because we would love to have an immediate gathering so we can thank people, but we decided, only because of Omicron and the COVID uptick, to wait,” said Gendreau.

In his last moments on Sunday morning, Winn was surrounded by family.

“Mom was right by his side the entire time,” said Gendreau. “It was precious.”

Like his community and his family, faith was important to Winn.

“We can take great comfort knowing where is,” said Gendreau. “He was a believer. He has Jesus Christ as his Lord and Savior, and he often spoke of that, and spoke of going home soon.”

Although the end had been nearing, Gendreau spoke of light moments and jokes shared between her father and his family during his last days.

“We know that he’s up in heaven, telling Jesus what to do with His town meeting,” she said.


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