Category Archives: The Boarding School Blog

Join us for our Open House this Fall!

Can you imagine yourself here? Come and find out!

Interested in finding out what it means to be a part of the Cheshire Academy community?

Check us out and imagine yourself here! We will be hosting two Open Houses this fall:

       Monday, October 15th, 8:30 am- 1:oo pm 

       Monday, November 12th, 8:30 am- 1:oo pm

A typical Open House schedule looks like this:

8:30 AM            Registration and Refreshments

9:00 AM            Welcome-Head of School

9:15 AM            Extended Campus Tour to meet various Department Heads

10:45 AM          Break & Refreshments

11:00 AM          Student Perspective Panel

11:30 AM          Faculty Perspective Panel

12:00 PM          Lunch

1:00 PM            Official Program Ends; Families are welcome to stay for our afternoon activities.

1:15 PM            Afternoon Options

  • Roxbury Program Overview
  • IB Program Overview
  • Class Visits: Math, English, History, Science

For more information or to reserve a spot, you can contact us in Admissions at 203.439.7250 or via e-mail at You can also register online. If you cannot make either of these dates, pick your own! We are happy to show you around and find you a few classes to sample. Directions to campus can be found here. We look forward to seeing you!

Check us out!

How will Cheshire Academy help me get into College?

If you are thinking about attending an independent school, chances are you also have an eye on the next big thing. So do we:


A Cheshire Academy student circa 1930–also gearing up for college!

From day one at Cheshire Academy, our faculty begins the exciting process of prepping you for life beyond high school; which is why they don’t just stand at the blackboard and write out long equations and vocabulary words while your fingers fall off scribbling notes (we use SMART boards!) When it comes to instruction, our teachers think beyond the board. Words and equations don’t mean much unless you use them. Which is why the majority of our classes are interactive and engaging; with a 12:1 student-teacher ratio, round-table discussions in class are expected. Field trips are a must. And applying your knowledge to real life scenarios is critical. We’re a college prep school, and we are here to provide you with the tools to succeed for when you walk across that stage, diploma in hand, and continue on to Boston University, Dartmouth, Elon, Hobart and William Smith, Brandeis, Union, Trinity, Penn State, Syracuse University, Brown, [enter your college here!]….

The CA Crest! Students and faculty wear this on their blazers.

Which brings us to College Counseling! Aside from our trained faculty who will prepare you for the critical thinking, writing skills, and independence that higher education demands, our College Counseling department is here to support you and your family as you contemplate what might be a good fit for you, create a customized college list, assist you with applications and financial aid information—and just talk about what your hopes are for the future.  You will be assigned a counselor who you will meet with you one-on-one throughout your junior and senior year; all of our juniors take an additional seminar on college preparation. During this nine-week College Counseling workshop, we expose you to an array of critical skills including resume building, personal essay development, mock admission interviews, and thoughtful discussions surrounding life after Cheshire.

Chat one-on-one with admission counselors–right here!

Though we will encourage you to explore colleges first hand and go on guided tours, we also host many admission counselors on campus for you to ask the questions and learn more about the various programs that colleges offer. Additionally, we host an annual College Fair, in which over 100 colleges and universities visit Cheshire Academy for a chance to meet with you. For more information on the many opportunities we offer in terms of college preparation, check out our resources page or feel free to contact us. You can also find important college counseling info and tips on twitter throughout the year– follow us @CheshireEd!

At Cheshire Academy, we stand by the motto, “College is a match to be made, not a prize to be won.” We care deeply about taking the time to cultivate our students and assist you and your family as you consider the next big step—after all, that’s exactly why we’re here.

You did it!

Welcome to Cheshire Academy!

Cheshire Academy is where YOU belong! Imagine a place where you engage in the discussions, you score the goal on the soccer field, you paint the image on the canvas, and you make a difference in a small, friendly, diverse community. If you would like to receive more information, you can request an admissions packet here or browse our website. We hope that our admissions blog will better help you to envision the many exciting opportunities that await you here at Cheshire Academy–because you are what makes this school great! Welcome!

Can you see yourself here? We can!