Answering your questions about all things CA!
These admissions resources are meant to help you explore more about Cheshire Academy and learn about all we have to offer. We’re also here to help you choose the best boarding school for you. We hope this helps you while you navigate the admission process, and as always, if you have an questions, feel free to reach out!
Cheshire Academy Admission Office
203-439-7250 | admission@cheshireacademy.org
Informational Fact Sheets
Want to learn about our programs, academics, and more? Explore our in-depth flyers to see how you’ll benefit from a Cheshire Academy education.
Admission Blog
Explore our blog and read more about navigating the private school admission process.
Frequently Asked Questions
Cheshire Academy accepts new students across all grades, 9-12 and postgraduate!
You can take up to eight classes per semester; however, most students average about six classes. It all depends on which classes and coursework you choose!
Interviews are meant to be conversational and a way for our Admission Officers to get to know who you are! Think about what interests you, and let us know – think academics, sports, arts, and music.
Cheshire Academy does not have specific athletic scholarships, but please check out our scholarships and financial aid page for more information on other options.
All day students are welcomed and encouraged to visit campus on the weekend. Day students are heavily integrated in our weekend activities, and are even assigned to dorms when they’re on campus!
All students (day and boarding) must be in attendance for our mandatory community weekends.
Boarding students are allowed to go home with proper permissions and communication with our residential life / dorm head staff.
All students (day and boarding) must be in attendenace for our mandatory community weekends.
Cheshire Academy Fun Facts
Our location was named one of the best places to live in the U.S.!
Cheshire Academy is located in Cheshire, Connecticut. Named one of the “Best Places to Live in the U.S.” by Money Magazine! Our campus is nestled in a picturesque Connecticut town featuring:
- Quintessential New England charm – safe, friendly, walkable
- Coffee shops, pizza, stores, and restaurants that make up our “extended campus”
- Convenient location halfway between New York City and Boston
- A quick ride to Amtrak and major airports
Did you know?
Cheshire Academy is the oldest boarding school in the State of Connecticut and the eleventh-oldest boarding school in the United States.
Cheshire Academy was founded in 1794!
Notable Alumni
Cheshire Academy prides itself on supporting our students become strong global citizens. Throughout our time, we have had many notable alumni pass through our halls.
A purr-fect mascot!
Cheshire Academy’s mascot is a Cat and he is sure to make an appearance at big events, games, and sometimes just walking down the hallway. You never know when you might catch him!
Have Questions?
203-439-7250
admission@cheshireacademy.org
