Jess Wilkey is a teaching administrator working the dual role of teacher and principal at the Woodstock School. Rose Lincoln, Bethel Citizen

WOODSTOCK — Jessica Wilkey, principal, is up before 6 a.m. and at the Woodstock School by 7:15 to sign kids in for breakfast. When “before school” is over, all the students line up by grade, and she dismisses them and their teaches to their classrooms. Next, she leads her own line of nine first graders to their classroom. Wilkey works in the dual role of Teaching Principal in this school of 62 students.

During “before school” the  cafagymatorium was crowded. Students no longer needed to qualify for free lunch. It was offered to everyone during COVID and that policy has stayed.

Wilkey listens to all kinds of questions from kindergartners to 5th graders, responding thoughtfully. To a fourth grader she sympathizes when he says his aunt is always busy. Then she responds, “she has a newborn. It’s a lot of work and it’s tiring.” A group of older boys gather around her as one shows Wilkey his book of sports cards. “Who is your favorite football team?” a different student asks. “The Patriots,” Wilkey responds.

Jess Wilkey is a teaching administrator working the dual role of teacher and principal at the Woodstock School. Rose Lincoln, Bethel Citizen

After her first graders order lunch – mac and cheese or pb & j – the class sits together in a circle for morning meeting then stands for the Pledge of Allegiance, all eyes on the flag.

“Ears listening, eyes watching, body still, mouth quiet,” Wilkey and her class recite together. One by one, the students take turns talking about their weekend while the others, using their listening skills, sit quietly. How to treat bloody teeth falling out of your mouth is a common theme during sharing time.  One student recommends swishing with salty water to stop the bleeding.

Wilkey tests their attention skills by playing “my turn, your turn” a game similar to “Simon Says,” but a little harder. They have to pay attention. She quizzes them on why they play the game. “It  helps with listening, focusing and self talk,” is one response. “Ignoring distractions is sometimes hard to do,” Wilkey reminds them. She reinforces the skills with a song they sing together. The lesson is part of a new curriculum in the district, called “Second Step” that teaches social and emotional skills.


After lunch, while some of the specialists, like the music teacher and physical education teacher, are working  with her students, Wilkey has a chance to catch up on her principal duties. If something urgent comes up when she’s in class, her secretary, Linda Yates, messages her and she finds someone to step in while she steps out.

With COVID funding, the district was able to support having a permanent substitute in the school who “floats” instead of the old system when they had to wait to call someone in if a teacher called out sick. “It’s nice to have someone who’s here and available all the time,” says Wilkey.

Being able to work one-on-one with the students in the classroom is a huge positive for Wilkey, although she says finding time to complete her administrative duties is sometimes challenging.

After school, parents arrive to pick up their children. Walkie-talkie in hand, Wilkie looks down the line of cars, calling by intercom to the teachers who should be released next. Busses come next and she keeps careful watch that everyone gets on safely.

After college at Northeastern University in Boston, Wilkey taught pre-school for two years, then decided to return home to Western Maine were she was raised. Her first job teaching elementary school was at Woodstock in 2006. She had a psychology degree so took the ETEP (Extended Teacher Education Program) program at University of Southern Maine to get her teaching certificate. The one-year program allows students to get their  education courses and student teach at the same time. About six years ago, she became an administrator. Of the longtime teaching principal who Wilkie replaced, Jolene Littlehale, she says, “She was a great mentor. She really encouraged me to take on leadership roles and continue my education.”

As to the present, “We’ve had really great opportunities for people to come in as volunteers or substitutes. They like it. And we’ve been able to encourage them.” says Wilkey, passing the baton she was passed.

“People from various backgrounds that maybe didn’t initially think they want to teach, then they get involved in the schools, and realize, I really enjoy this,” says Wilkey. Asked about her previous position as the kindergarten teacher, she says, “We have a new kindergarten teacher; she was a long-term substitute.”

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