Enroll for this fall!

Local families, are you worried about what school will look like for your child this fall?

We have heard countless stories from parents who have bright students who lost ground in the spring and will now fall behind even more. Maybe you’re concerned your child won’t be ready for what comes next.  

Cheshire Academy has opened safely — in person — this week. We have plenty of space, strict health and safety measures, a new weekly schedule designed for in-person and for remote learning, and the academic challenges and support students need to thrive.

It’s not too late to apply for the fall semester, but the window of opportunity is closing fast. Click the button below to fill out our short inquiry form and a member of our Admission team will be in touch soon.




View our schedule


We have created a weekly schedule that takes into account the need to provide for both remote and in-person schooling. Our schedule includes larger blocks of time that meet fewer times per week.The schedule accommodates health and safety guidelines to keep our community safe without sacrificing opportunities for extra help, one-on-one support, and student engagement through advising groups, clubs, class meetings, and student activities.





Academic Programs


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


Signature Programs


Many schools boast about programs that make them stand out. At Cheshire Academy, however, our signature programs are distinct and designed to set you—the student—apart.


  • Earn college credit through the International Baccalaureate® (IB) Programme
  • Get 1-to-1 support through the unique Roxbury Academic Support Program 
  • Develop a complete portfolio for the college admission process in the Art Major Program 

Don’t let your child fall behind this school year. 


Fill out the short form below and a member of our Admission team will be in touch soon.