PITTSFIELD, Mass. — Superintendent of Schools Jason "Jake" McCandless is actively seeking new opportunities and may leave the Pittsfield Public Schools.
After McCandless' evaluation by the School Committee on Wednesday, he confirmed that he is a finalist for the superintendent's position of the Silver Lake Regional School District in Kingston, just north of Plymouth.
"It simply feels in my gut like it is a good time to make a change," McCandless said.
McCandless came to Pittsfield in 2013 after being in Lee for 11 years, eight of those as superintendent and three as principal. He came to Lee after three years as an assistant principal in Virginia.
He signed a six-year contract in 2015, setting his salary at $157,000. The Silver Lake post would pay between $170,000 and $190,000 and the selected candidate would be expected to begin when the current superintendent retires at the end of January. Silver Lake has about 1,800 students compared to Pittsfield's 5,400.
"There are hundreds of things I will miss about Pittsfield and the Pittsfield Public Schools," the superintendent said on Thursday. "The wonderful people who make things work in the city and county and our students are an honor and privilege to serve as are their families."
He went on to praise the School Committee, the staff, city leaders, and the larger community that has supported him through the years.
"We have dedicated employees across the entire organizational chart and wonderful families who trust us with their treasure each day," McCandless said. "Our city government takes education seriously, and our whole county works together in extraordinary ways. Serving Lee, Tyringham, and Pittsfield has been a gift to me and our family.
"I will miss so much. I could go on, and talk myself out of this altogether."
McCandless said if not selected he and his family will re-evaluate their options. He said remaining in Pittsfield is not out of the question.
"If this opportunity does not work out, our family will evaluate our options and see," he said. "Staying here and continuing to serve is an excellent scenario, so we will see."
During his evaluation, the entire School Committee lauded his efforts over the years and all gave him marks of "exemplary" and "proficient."
Member Daniel Elias said he was astounded by his work ethic and dedication and member Joshua Cutler applauded his leadership especially during the school building project and rough budgetary times.
"His leadership comes at a critical time in Berkshire County as we face population decline, demographic shifts, and a lack of growth in resources that has dictated difficult decisions."
Members William Cameron and Dennis Powell thanked McCandless for his efforts to create a tolerant and inclusive environment in the school system. Powell said when he was the president of the NAACP, McCandless was completely receptive to all their concerns.
"These are difficult times and it is very difficult to change behavior and change mindsets," Powell said. "He did not give up on that ... he understands what it takes to make change."
Mayor Linda Tyer also had good things to say about McCandless and said he is a great communicator and advocate for students.
"Pittsfield is beyond fortunate to have Dr. McCandless leading our school community," she said. "He confronts challenges head-on and with passion and celebrates outstanding staff and student performances."
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Pittsfield Schools Finalizing Bus Routes for Fall
By Brittany PolitoiBerkshires Staff
PITTSFIELD, Mass. — The district currently has enough bus drivers for the upcoming school year, and families will know their child's transportation schedule in mid-August.
With about five weeks left of summer vacation, Superintendent Latifah Phillips updated the School Committee on transportation for the 2026-2027 year with middle school restructuring and the closure of Morningside Community School.
Busing is a question that has continuously been raised as the Pittsfield Public Schools approach an academic year with a couple of big changes.
"The reason that the bus stops and times aren't shared until very close to the school year is that routes change based on every student that moves into the district and requires a bus, and so it's important for us to wait as late as possible to ensure that families are getting the most accurate timetable," Phillips explained during a meeting held at Reid Middle School on Thursday.
"We are also continuing to explore after-school transportation for the four schools receiving Morningside, and a survey was given to students who attend the Summer Morningside 21st Century Program to assess transportation needs."
That survey found that transportation does not appear to be a big impediment to students participating in the after-school program, but funding is set aside to ensure students are able to access the same services as they were the previous year.
The district is still planning to offer after-school programming for Morningside transfer students, and is working with the four receiving elementary schools (Allendale, Egremont, Williams, Capeless) to plan a practice bus ride.
Phillips explained that, for someone who has never ridden a bus before, and especially a school bus, they want to ensure that students are poised for success and understand the rules and expectations before the first ride. Students will be able to get on the bus, ride the route, arrive at school, have a quick break, maybe play on the playground and have a popsicle, then return home on the bus.
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