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Matt Roy Selected as Next Thomas Fleming Principal

May 7, 2020
Video Q&A with Roy
- Matt Roy has been chosen as the new principal at Thomas Fleming School. Roy will take over for current Principal Dan Ryan, who will be retiring at the end of the current school year. 


“I consider Essex Westford School District lucky to have Matt Roy joining us as principal of the Thomas Fleming School. Matt brings experience as a classroom teacher and assistant principal, as he is passionate about Professional Learning Communities (PLC) and understands the value of having teachers work in teams,” said EWSD Superintendent Beth Cobb. “Matt relates well to students and will be a positive role model for them. I am looking forward to having him join our EWSD leadership team.”


An educator in the state of Vermont for the previous 13 years, Roy has spent the last four at Main Street Middle School in Montpelier where he was the assistant principal and also the school’s athletic director for one year. 


Prior to his time at Main Street Middle School, Roy taught social studies for grades five through eight at Berkshire Elementary from 2011-2016 and was also the school’s assistant principal during his final three years there. 


He held many different leadership roles while he was at Berkshire, which included being a curriculum council member for the Franklin Northeast Supervisory Union, a PLC team leader, and an eighth grade advisor. 


"I am really excited to be joining the Essex Westford and Thomas Fleming communities. From what I know about Fleming, I feel honored to be joining a fantastic school community,” said Roy. “I look forward to the time when I can meet staff members, students and families in person."


He attended Western New England College as an undergraduate, while also earning a master’s in education from St. Michael’s College. Roy has previous experience in what is now the Essex Westford School District, as he spent time as a student teacher in the fall of 2009 at Essex Middle School while earning his master’s degree. 


Roy will officially start at Thomas Fleming on July 1, 2020.




Connect With Your New Principal! 


With the current state of affairs and the Stay Home, Stay Safe order in effect, Fleming is unable to host an in-person meet and greet with the new principal. Students, parents, and community members will have a chance to ask questions for an upcoming video interview that will be shared publicly in the meantime. 


If you have a question that you would like to ask, please submit that to Essex Westford School District Communications Coordinator Ben Dickie ( by Tuesday, May 12.