Jason “Jake” McCandless’ arrival as the new superintendent for the Mount Greylock Regional School District comes amid a worldwide pandemic and just as the district furiously is figuring out how to conduct schooling during an unprecedented challenge.

WILLIAMSTOWN — Jason “Jake” McCandless was appreciated immensely in Lee as superintendent of schools for eight years. Then he moved north, to steer Pittsfield schools through several crises, including the coronavirus pandemic, for seven years.

When he resigned both jobs, he left behind some broken hearts and many friends.

Now, he has landed in Williamstown to helm the Mount Greylock Regional School District, to complete what some might call the triple crown of Berkshire County superintendencies.

“Everyone has been incredibly welcoming since my first day,” McCandless told The Eagle.

His arrival comes amid a worldwide pandemic and just as the district furiously is figuring out how to conduct schooling during an unprecedented challenge, with some urging more in-school instruction and others seeking all-remote learning.

McCandless faces other issues that have been percolating, including the debate about artificial turf versus natural grass for the playing field at Mount Greylock Regional School, which also has proved to be a divisive topic.

The district leadership has been in transition, ever since former Superintendent Kim Grady left on indefinite medical leave in June, and then the short term of interim Superintendent Robert Putnam, who kept the ball rolling since July.

McCandless arrived for duty Nov. 2.

He said he loves what he has seen so far.

After a couple of days on the job, McCandless said he mostly has been exploring the schools, having visited Lanesborough and Williamstown elementary schools and the middle/high school.

“I’ve been getting to know the district and the wonderful people here,” he said.

Already, he said, he feels gratitude for the work done before him by Grady — she worked through the construction of the new school and unifying three districts into one — and Putnam — he has been holding the ship together through most of the pandemic — for leaving the district in good shape and ready for the next steps forward.

“All that heavy lifting was done well by Kim Grady,” McCandless said. As a result, he noted, “Mount Greylock is one cohesive unit with three very special schools.”

One of the first jobs McCandless will face is wrapping up the budget for the coming school year.

“Making sure we have the resources to do our work is a priority,” McCandless said.

McCandless started in public education in 1993, and has served as an alternative education program director, English teacher, football and wrestling coach, department chairperson, assistant principal, principal and superintendent. His career spans public school service in Pennsylvania, Virginia and Massachusetts.

He is a graduate of Grove City College in Pennsylvania, with degrees in Literature and Communications, and earned a master’s degree from the University of Virginia and a doctorate in Educational Leadership from Boston College.

According to Mount Greylock School Committee chairwoman Christina Conroy, “We received numerous endorsements for Dr. McCandless from the Berkshire County community. [Former committee member] Al Terranova said in our discussions that McCandless was his top choice and noted the strength of his positive references, specifically from the Mayor and Chief of Police of Pittsfield.”

She noted that former committee member Jamie Art gave McCandless the edge over the other interviewed candidates because of his demonstrated history of longevity in other districts and “his emphasis on humanity, dignity, compassion, respect and deep roots in the community.”

“I myself noted the universally strong feedback we’d received for Dr. McCandless and his direct exposure to COVID planning within a school district,” Conroy said. “For all the reasons mentioned above, Dr. McCandless is the right choice for our district. We feel fortunate to have him on board and can’t wait to see where he leads this district.”

McCandless, 49, said he is here for the long haul.

“I’m really hoping to finish my career here, in a district with 1,100 students, where I can get to know everyone,” he said. “What has always driven me as an educator is the people I get to work with and the children I get to know, and making school the best it can be for every single child.”

McCandless said he decided to leave Pittsfield Public Schools when it became apparent that it was time for some new thinking.

“It was hard to leave Pittsfield and the hundreds of people I got to know,” he said. “But, it’s important for a leader to be able to look away and realize that it might be time for somebody else to bring in new ideas and new ways of doing business. I’m still sad about leaving Pittsfield, but what an absolute pleasure to come here.”

Scott Stafford can be reached at or 413-629-4517.

Scott Stafford has been a reporter, photographer, and editor at a variety of publications, including the Dallas Morning News and The Berkshire Eagle. Scott can be reached at, or at 413-496-6301 and on Twitter at @BE_SStafford.