Cheshire-logo (002)

Founded in 1794, Cheshire Academy is one of the oldest boarding schools in the country. A coeducational boarding and day school serving students in grades 9-12 and post-graduates, the Academy sits on 104-acre campus, located in the Historic District of Cheshire, Connecticut.  There are more than 350 students representing over 30 countries and 20 states, providing a community atmosphere that is rich with diversity.

Cheshire Academy is an internationally minded college-preparatory school that challenges its students to maximize their potential by developing the confidence, character, and critical-thinking skills that enable them to thrive as global citizens. Our students grow increasingly capable of independently observing, questioning, explaining, interpreting, and analyzing the world.  The Academy puts the unique needs of every student first and offers a flexible program that allows students to mix academic course tracks with athletics and/or fine arts programs, according to their needs and interests. Students participate in a rigorous academic program that provides for personal attention and support in small classes. Among the many academic offerings, students may choose to enroll in the International Baccalaureate® Diploma Programme.  Cheshire Academy is the only private school in Connecticut to offer this globally recognized high school diploma. Another signature program is the Roxbury Academic Support Program, which provides several types of educational coaching for students who need assistance outside of the traditional classroom.

A key part of the academic program is a focus on the arts. With a wide range of offerings, including visual arts, dance, drama, music, and digital arts, students can delve into the creative mediums that interest them most.  The Academy even offers an Art Major program for student artists looking to pursue art beyond high school. Art Majors are given studio space and work with instructors to build quality art portfolios.

Academy students also participate in a comprehensive afternoon program that includes competitive and noncompetitive athletics as well as a variety of other team-based initiatives including drama, community service, and a communication team internship. Cheshire Academy has produced professional athletes as well as countless collegiate athletes. With over 20 sports teams for boys and girls and many afternoon options, there is something for everyone.

To learn more about Cheshire Academy or to complete your application for admission, visit us online at