Great Barrington — At the Berkshire Hills Regional School District Committee’s meeting on Thursday, January 15, W.E.B. Du Bois Regional Middle School Principal Jake McCandless announced his intent to retire by the end of the school year in June.
McCandless, originally from western Pennsylvania, took the position back in the summer of 2024 after previous principal Miles Wheat left the school district to become the principal of Chatham High School in New York.
McCandless has worked in education for 33 years, starting as an English teacher in Mineral, Va., before moving to Berkshire County with his family. Before his time at Du Bois Middle School, he served as the principal of Lee Middle and High School, the superintendent of the Lee School District, the superintendent of the Pittsfield School District, and, most recently, the superintendent of the Mount Greylock Regional School District.
“To me, there’s nothing more important than what happens in a school classroom,” McCandless said in an August 2024 interview with The Berkshire Edge. “If you were completing an organizational chart from the most important, crucial people in the building of a child’s daily life, the custodians, the cafeteria workers, the paraprofessionals, and the teachers would all be well above the principal and the assistant principal. Our work is to support the work of everybody else to make their jobs easier, more efficient, and better and to help them better understand their work if the need is there. I felt that—early on in my career, I felt a need to be more involved in the systems and support of helping great teachers do their work, rather than digging in and becoming a great teacher myself. I decided to put my energy and my efforts into supporting individual people and supporting systems that hopefully make schools work as well as they can for young people and for the people we’re all here to serve.”
On January 16, 2025, the school district announced that it had extended McCandless’s contract through June 2028.
However, at the January 15 meeting, Superintendent Peter Dillon said that McCandless would be retiring. “I think the world of Jake,” Dillon said. “He stepped into the [principal] role from being a superintendent. He put his heart into Du Bois [Middle School], and he stabilized it and still has a smile on his face. It’s way too early to say goodbye because we have another five months left with his skillful leadership.”
“My heart will very much be with Du Bois [Middle School],” McCandless said. “As you can tell from watching me walk up to the [meeting] table and back again, my hips and knees are on a different planet, and the rigors of keeping up with 330 middle schoolers are just about more than I can do on some days. But my heart very much remains at the school, and I’m incredibly grateful for two amazing years of getting to be part of that school.”
