Admission Events

Join us for one of our upcoming online admission events.


To receive details about upcoming events please click the button below and fill out the short form.




Cheshire Academy is the first independent high school in Connecticut to lower tuition! Learn more at our online events.





Students grow increasingly capable of independently observing, questioning, explaining, interpreting, and analyzing the world. Our academic process begins with what students know and want to know, and develops active learners who reflect on their growth and the implications of their learning.


    • 6:1 Student-to-faculty ratio
    • 119 course offerings
    • 81% of faculty have advanced degrees 


College Counseling


Our professional college counseling team is dedicated to finding the school that is the right fit for every student. College counselors help guide students through every facet of the college search process, including researching schools, registering and preparing for standardized tests, visiting college campuses, writing application essays, and navigating financial aid. 


    • Highly personalized process starting freshman year
    • More than 200 colleges on campus annually
    •  99% of Academy graduates attended selective colleges and universities





The athletics program offers boys and girls opportunities to develop their skills or try something new. There is also a range of non-competitive athletic activities, all focused on team building, competitiveness, wellness, fitness, and pride in contributing to a team.


    • Helped hundreds of student-athletes reach their goal of competing in college athletics
    • 15 athletic championships over the last 10 years
    • 21 interscholastic sport offerings




Our historic 104-acre campus is nestled in the bucolic but central town of Cheshire, Connecticut, just two hours from both Boston and New York City. Though Cheshire Academy provides everything students might need on campus, students are welcome to explore the nearby Cheshire extended campus during their downtime.


    • Two-hour drive from Boston and New York
    • Walking distance to downtown Cheshire
    • Short drive to the culture and vibrancy of New Haven (home of Yale University) and Hartford

International Baccalaureate® (IB) Diploma Programme


We are the only independent school in the state to offer the International Baccalaureate® (IB) Diploma Programme—recognized as the leader in international education. All students take at least one IB course during their time at the Academy and some earn college credit.

Postgraduate (PG) Program


Cheshire Academy offers a comprehensive Postgraduate (PG) Program. A robust academic experience, the PG program is an opportunity for students to build upon their skills, improve their academic portfolio, and prepare for their next step of attending college

Academic Support


The goal of the Roxbury Academic Support Program is to develop proactive, knowledgeable, and independent learners who take responsibility for their education and academic success. Roxbury alumni graduate feeling confident and fully prepared for the demands of college. Our unique one-to-one program is designed to strengthen the ability of our students to discover, master, and utilize tools and strategies that allow them to become more productive learners.



Registering is easy:


1. Fill out the short form below. 

2. Click “submit.” 

3. Our Admission team will email you with information about our next admission event.