Chester Academy Principal

  • John Flanigan, Principal



  • I am both excited and focused on working with our students, staff, and community members here at Chester Academy as we look to start the 2022-23 school year.  As I begin my fourth year here in Chester, I look forward to a year that is student centered, future focused and team driven. The Chester Community is truly a special place, and I am grateful and humbled to have the opportunity to continue to work with your children.

    I have spent the last twenty years working in education as a teacher and building level administrator in Orange County. I received my Master’s degree from Mount Saint Mary College with a concentration in Adolescent Education at the secondary level.  After seven years of teaching social studies, I completed an Advanced Certificate in Educational Leadership from Long Island University, and I have been working as an Assistant Principal, Dean of Students, and Middle School/ High School Principal.  I am looking forward to once again working with our administrative team, teachers, support staff, parents, and community to ensure our students have a great school year.  I have always believed that a great school is the result of a team effort.

    I have a passion for helping students succeed.  I believe in challenging our students to create problem solvers as well as fostering an environment that facilitates lifelong learning. Every student should feel they have the ability to succeed and fulfill their unique potential.

    I am looking forward to seeing the members of our community, and most importantly, having the great responsibility of educating your children.  The 2022-23 school year is going to be a great year.  Feel free to contact me if you would like to discuss any concerns, or just to say hello.  My door is always open. 


    John J. Flanagan
    Chester Academy Principal