Chester Academy Principal

    CHESTER, NY 10918


    I am both excited and honored to be selected as the new Principal of the Chester Academy.  Since my appointment earlier this month, I have been greeted by many warm and welcoming students, staff, and community members.  The Chester Community is truly a special place, and I am grateful and humbled to have the opportunity to work with your children.


    I have spent the last sixteen 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 both an Assistant Principal and Dean of Students.  I am looking forward to working with the administrative team, teachers, support staff, parents, and community to ensure a smooth transition.  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 life long learning. Every student should feel that they have the ability to succeed and fulfill their unique potential. 


    I am looking forward to meeting the members of this community, and most importantly, having the great responsibility of educating your children.  The 2019-20 school year is going to be 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

John Flanagan