In the public eye: Wescott to leave legacy of positivity at Windham Middle School

Editor’s note: This is another in an ongoing series of Windham and Raymond town employee profiles.

By Ed Pierce

Somewhere early in his teaching career, Bill Wescott learned that by being positive and helping his students to succeed, he too could succeed. It’s a philosophy that’s worked for Wescott for 46 years in his career, one that draws to a close with his retirement on June 16.

Bill Wescott will retire from teaching at Windham Middle
School after 46 years on June 16. During his long career as
an educator, Wescott has taught between 4,000 and 5,000
students by his estimation. He is the son of the late former
Arlington School Principal Robert Wescott and his wife,
Jean, who was also a teacher. PHOTO BY ED PIERCE  

He began his teaching career as a substitute with a long-term assignment filling in from November 1976 to June 1977 at Field-Allen School and then landed a permanent job at the newly built Windham Middle School when it first opened that fall. Wescott has been there ever since, teaching History and Social Studies to eighth grade students, although this year shifting over to teaching seventh graders Language Arts and History. By his own estimate, he’s now taught between 4,000 and 5,000 students in his classroom and says that he’s had the best job in the world.

As the son of two teachers, Jean and Robert Wescott, he grew up in Windham and graduated from Windham High School in 1972. He returned to town after earning a Bachelor of Arts degree from the University of Maine at Orono and credits Gary Moore, his first principal at WMS, as seeing something in him and offering him a job that has now lasted nearly five decades. During his long teaching career, Wescott has worked for five principals at WMS, including Moore, who was an English teacher when he attended Windham High and then later served as the Windham Schools Superintendent.

“To me, this is the best job in the world,” Wescott said. “No two days are alike. There’s a lot of energy in this place and the students really haven’t changed a lot. Some of the technology we use to teach them has changed and made it much more kid friendly.”

From 1977 to 1998, Wescott also served as a coach for three different sports, coaching girls’ JV soccer, middle school girls’ basketball and JV softball, with one season spent as the Windham High varsity softball coach. In the classroom, he’s helped students explore the history of America up through the War between the States era, although now he just covers from about the French Indian War in the 1700s up to the Civil War.

What makes him an exceptional classroom teacher is his innate skill of relating to his students.

“I have the ability to connect with the shy and quiet kids and bring them out of their shells,” he said. “Patience is so important for a teacher, especially since so many kids fell behind during COVID.”

Many of his former students have gone on to become teachers themselves, including more than a dozen alone at WMS this year.

According to Wescott, the thing he will miss the most about teaching is interacting with the kids.

“You have to expend a lot of energy to keep up with them,” Wescott said. “And it’s not easy trying to keep them energized. We’re teaching them what they need to know but also what they want to know.”

Of his siblings growing up, Wescott said that he is the only one of three boys and a girl in his family to follow in his parents’ footsteps and become a teacher.

“For some reason they didn’t want to do that,” he said. “In fact, most people don’t want to be a teacher.”

Through the years Wescott has had generations of students, who easily recognize him at the grocery store or while out shopping in Windham.

“One time a mother and a student walked by me, and the mother got this look on her face that she instantly remembered me,” he said. “Later that student told me his mother said she couldn’t believe that I was still teaching. She told him ‘Mr. Wescott was old when I had him.’”

His plans for retirement are to work as a substitute if needed in the fall. His mother is now 90 and he expects he’ll spend some time helping her too.

“I’ll figure it out,” Wescott said. “I always said I’ll know when it’s time to retire and it’s time. I have a cat and I’d like to travel and work on some hobbies.”

His advice for those wanting to follow his career path as an educator is simple.

“Students don’t remember what you taught them but how you made them feel,” Wescott said. “Be positive, make them feel good about what they can do and give them confidence.” <