Shawn Gallagher, a Whitefield resident who works in Southport, couldnt be happier to have a hand in both communities. Friends told Gallagher about Whitefield long before he moved there and he said he knew he wanted to be a part of the Southport Elementary School virtually from the minute he laid eyes on the place. (Sherwood Olin photo)
Shawn Gallagher still remembers his first impression of the Southport Central School. While waiting to interview for a support staff position in 2013, it was suggested Gallagher observe lunch when his scheduled interview was delayed a few minutes.
Pressed into service, he watched as the head cook, Southport legend Ramona Gaudette, served lunch. Gaudette worked at the school for 57 years before retiring around 2012.
“I’m watching the kids come through, and she gives them their lunch,” Gallagher said. “She comes out from behind the kitchen, and she goes and kisses every kid on the head. At the end of lunch, the kids are leaving and she’s telling them she loves them and giving them hugs. And I thought, sign me up. At that point, I was like, this is home.”
It was a fitting start to an association that Gallagher maintains to this day as the Southport Central School principal. He got the staff position and the next year was hired as teacher for grades four, five, and six. He stayed in that position for the next eight years.
At the time Gallagher was living on River Road in Newcastle with his wife Elizabeth, but by then the couple had fallen in love in with Whitefield. The Gallaghers had friends in the area and Shawn had been convinced of Whitefield’s charms years earlier by coworkers who lived in the town.
They eventually bought some land away from the village, built a house, and relocated before welcoming their first child, Arthur, in 2020. Gallagher acknowledged having some misgivings about increasing his commute with the move, but said every mile has been worth the effort. On a good day the 42-mile commute takes about 48 minutes, he said.
“The whole time, we kept saying, ‘Am I going to keep commuting to Whitefield?;” he said. “I’m driving from Whitefield to Southport to be a teacher, but the more I did it, the more thought ‘I can’t leave this place. I can’t leave this place at all.’”
Reluctantly, Gallagher did take his leave in 2021, prompted by a need to stay home with his infant son. During his hiatus from teaching he and Elizabeth worked on their home and started a microfarm with his brother Ron, eventually selling produce to about 15 community-supported agriculture programs and a handful of restaurants.
“We wanted good food for our family, and we wanted to start building these routines of a relationship to our food,” he said. “There’s no better place to know where your food comes from than where there’s farms all over all over the place.”
Gallagher left Southport not knowing if he would or could return. As it happened, the Southport principal’s position just as he reentered the work force in 2024 and he eagerly applied for it.
While a principal’s position is frequently a stepping stone to school district administration, Gallagher said he has no interest in management on that scale. It would take him too far away from what he loves about the field, which is the kids and the relationships that makes education work, he said.
If anything he would go in the other professional direction, he said, back into a classroom teaching role.
Shawn Gallagher poses with his son Arthur, 5, on the first day of school in September 2025. Arthur is enrolled in kindergarten at the Southport Central School where his father is the principal. (Courtesy photo)
A Chelsea native, Gallagher graduated from Cony High School and went on to attend the University of Maine Farmington. He had planned to pursue a career in community health education, but while he was in college he started working for Dick’s Sporting Goods. By the time he graduated from UMF in 2002, he was a sales manager clearing $45,000 a year, heady money for young man with few commitments in 2002.
It didn’t take long before Gallagher realized he wanted something more out of life, he said. By 2008 he obtained his teaching certificate and went to work teaching special education at the Spurwink Services in Chelsea.
It was a challenging position but one that proved infinitely valuable in that he learned lessons about people and relationships that he uses to this day. During that same period he and friend bought a bar in Hallowell, and Gallagher moved in upstairs.
“It was that time in your life where you just can do anything,” he said. “So I was teaching, and I owned a bar with my friend, and we owned it for a couple years. Then I just I realized it’s too much. It’s too much.”
In 2012, he sold his interest in the bar, sold or gave away most of his possessions, packed up what he needed into his truck and took off on a road trip throughout the western United States. He was the road for the better part of a year.
Gallagher wasn’t really looking for anything, he said; he was just looking. Flush from the sale of his business he was able to live in his truck and survive on a shoestring.
“It’s that time in life where you do something like that, and have that experience,” he said. “Sleeping wherever you can really. That was it. It was just hiking, being in the woods, writing, reading, talking to cool people, meeting cool people … The greatest thing was the time that I spent slow, you know? If I wanted to be in a spot, if I wanted to stay in the Black Hills for two months, I’d stay in the Black Hills, and I could read and write, everything that I wanted to do.”
Looking back Gallagher doesn’t speculate now on what he could have done or might have done, but he does acknowledge that he came back to Maine specifically for one reason. Three months before he left in 2011, he met the then Elizabeth Bancroft, the woman who would become his wife in 2015.
The two bonded over a shared love of adventure, being active, and the outdoors. They met at gym in Hallowell owned by Gallagher’s brother. During Gallagher’s sojourn, Elizabeth came out to visit him a couple times and he was glad to come back to home to her.
“Elizabeth has always been adventurous,” he said “She wants to go do, really. She’ll do the back country camping. She’ll do the hiking. She’ll do the skiing. These are all things that made us fall in love in the first place. We’re doing it as a family right now; you know, smaller scale, of course. It’s a smaller back country with the kids.”
Last December the couple managed a brief getaway, their first since their second child, Theo, arrived in 2023. They took the opportunity to drive to Millinocket and run a half-marathon together.
“My wife said we need to start figuring out better date nights, because that was our first real night away from our family,” Gallagher said. “It was cold – cold, cold, cold.”
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