New principal brings small-school affinity to Harpswell

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HARPSWELL — The Harpswell Islands School is getting a new name, the Harpswell Community School, and a new principal, Kerry Bailey.

Bailey, 59,  is anything but new to school administration. This will be her third job as a principal, and her family is filled with other school administrators and teachers.

“I am surrounded by educators,” she said, laughing.

Bailey’s husband, Steve Bailey, is becoming superintendent of schools in Damariscotta, and used to be assistant superintendent in South Portland. Her sister was a principal in Wiscasset, and her father was a teacher.

Bailey started out as a teacher, and made the jump to school administration when she was 32. After teaching elementary and middle school in Portland and Yarmouth, she became the principal of Yarmouth Intermediate School in 1984. She stayed for four years before transitioning into staff development, which she says is her strength.

“My most comfort now is working with adults who are working with children,” she said. “I really like coaching in the classroom and helping teachers with differentiation in their instruction, helping them relate to kids if they’re struggling.”

Bailey became a principal again in 2003 at West Bath Elementary School, and stayed for two years before leaving to become a contract employee for the Department of Education. She’s currently working at Lisbon High School as a literacy coordinator.

While she loves her current job, Bailey said the insecurity of the position was getting to her. “It’s hard to find consulting jobs,” she said, and when she does, her position is often one of the first to be eliminated during budget cuts.

She said she is looking forward to taking the helm at the Harpswell Community School, which she said is similar in size and age group to her previous school in West Bath. She said she especially enjoys working at small community schools.

“I think they’re very special,” she said, partially because they are becoming a rarity.

Bailey said she was sensitive to the fact that Harpswell just lost one of its elementary schools.

“There’s a grieving process that happens when you lose a school,” she said. “It will be a challenge to preserve some traditions and to have (the West Harpswell School children and parents) feel totally welcome and involved.”

But she also believes there are unique opportunities created by school closures. She said she has worked with school communities in this situation in the past and in her experience, parents and teachers “discover some real strengths in one another and tend to be surprised.”

Although she had heard that some town residents are interested in withdrawing from School Administrative District 75, she said she hasn’t formed an opinion about that possibility. But she encouraged Harpswell parents to tell their students they are going to have a good year in school.

“Children need to hear that,” she said. “They need to carry that message to their kids so it get carried to school.”

Bailey said she is looking forward to jumping back into community schools, but she is also excited to work closer to where she lives. Since leaving West Bath, she has been working in Lisbon and commuting around the state.

She and her husband are “excited about digging in and having our roots here where we work,” she said. “We love it up here, we love the people.”

Emily Guerin can be reached at 781-3661 ext. 123 or eguerin@theforecaster.net. Follow her on Twitter: @guerinemily.

Sidebar Elements


Kerry Bailey is the new principal of Harpswell Community School.

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