Resources and updates for the 2023-2024 school year are available here


Our professional college counseling team is dedicated to finding the school that is the right fit for every student. While college “placement” is the term often used, college options, selection, and best match are the goals we persistently pursue.

College counseling is one of the true distinctions of a Cheshire Academy education. Here, you’ll benefit from a comprehensive, four-year process dedicated to finding the right college fit for you.

We have three full-time college counselors who are fully immersed in our students’ day-to-day experiences, who also serve on campus as coaches, advisors, and dorm parents. They’ll know you very well and provide you and your family with uniquely personalized guidance through each step of the college search and application process.


It can feel overwhelming to think about how to navigate the college admissions process, from choosing the right college or field of study, to filling out an application and writing a college essay.

Luckily for our students, Cheshire Academy’s College Counseling Office provides–bar none–the strongest scaffold of support and guidance you can hope for starting at the very beginning of your school journey here.


Get prepared for college by meeting some of 125 college representatives hosted by CA each fall. Catch an on-campus college fair in the spring for juniors and seniors. Get future-ready as we prep students for interviews, college visits, etc. As a senior, you’ll put the finishing touches on your college applications in a mid-October workshop with faculty and college counselors.


While the college search can be a challenging and sometimes confusing experience, our students and families can be assured that professional advisors and a proven college counseling program are there to guide you confidently and successfully every step of the way.


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. Students meet one-on-one and in small groups with their counselors, who act as confidants and guides.

Counselors get to know each individual student they work with, carefully understanding and even challenging their aspirations and priorities. They tailor their support and provide a wealth of information necessary to navigate the college application process.


We are committed to supporting students and their families alike, through an open, honest, and transparent way while navigating the college process.

While it can be a challenging, time-intensive and sometimes confusing experience, students and parents/guardians are assured there is a professional advisor at their side and an effective college program at Cheshire that will help guide them to what is best and appropriate for the next phase of the student’s academic career.

For Students

College Counseling

College Admission Seminars
The college counselors facilitate a series of seminars about the college admission process beginning in the freshman year and continuing through their senior year. College admission seminars for postgraduates are included in their Postgraduate Seminar course.
College Counselor Relationships
We assign sophomores to college counselors in January and meet both individually and in small group sessions through the year. We continue to meet with students into their junior and senior years. We are counselors and confidants; we are a resource of information from the onset of the testing process all the way to financial aid and final college selection.
College Representatives on Campus

Cheshire Academy welcomes over 125 college representatives from all over the world each fall, between the months of September and November, to meet with our students in one-to-one and small group sessions. These meetings serve as a hub for question-and-answer periods and a place to informally gather information with representatives knowledgeable about the admissions process.

In the spring, Cheshire Academy is host to a spring college fair, which draws over 200 agents from colleges and universities. Sophomores and juniors attend, with juniors participating in mock interviews with college spokespeople.

Throughout the year, students are also able to register for virtual open houses and panels at various colleges. CA’s college counselors also attend presentations and fly-ins at colleges all over the world, staying up to date on college application and admissions trends.

Parent Involvement

We involve parents in every part of the process. We also send important emails directly to parents about critical events or dates in the admission process. At Cheshire, we take a holistic approach to finding the best fit for each student; while many students enter our office with an idea of what schools they would like to attend, part of our role is to encourage students to read, explore, and evaluate a larger range of well-matched colleges. Through our hands-on College Counseling process, we inform and support students and their family during this important life milestone.


Grade 9
This first semester session focuses on what all students should be doing their four years of high school. This session is NOT about college choices but about the focus on academic preparation, involvement, and activities in high school.
Grade 10
The Road to College, Part 1
This second-semester session focuses on those components of the college admission process that students can directly affect or control, such as academic and test performance, community involvement, and extracurricular participation, as well as what criteria colleges and universities weigh when making admission decisions. We also discuss the importance of maximizing academic strengths in the context of a broad high school curriculum

The Road to College, Part 2
Sophomores establish an account on Naviance, the password-protected Internet site that houses our complete admission data and from which students can research colleges, admission criteria, a career survey, etc. Once they have registered, sophomores have the responsibility of completing the Career Interest Inventory on the “Do What You Are” component of the web site.
Grade 11
Cheshire Academy’s College Counseling process is heavily focused on the junior year. Some sessions are covered in two meetings.

Introduction to College Admission
This session covers the broad aspects of the college process, such as college search and admission jargon, financial aid, learning how to estimate predictability of admission, and the emphasis that CA’s College Counseling Office places on the “FIT.”

SAT and ACT Registration
Counselors direct students on test registration procedures. Registration forms are initiated online and students are able to finish them later if necessary. All sophomores take the PreACT in October, all juniors will take the PSAT in October and the School Day SAT in March. Cheshire Academy is an official SAT test center, offering 2019-20 tests on Nov. 2, Dec. 7, and May 2.

The College Admission Process, an in-depth review
This session covers the components of the college admission process including standardized testing, teacher and counselor letters of recommendation, essays, review of the high school transcript, the campus visit, more on financial aid and scholarships, tips for working with your college counselor, resumes, athletic recruiting, tips for making the most of a college fair, and the college interview.

The College Admission Essay
This session addresses the college essay. Sample essays are reviewed and additional resources for advice and expertise are cited and discussed.

Financial Aid and NCAA Eligibility This session serves as an introductory lesson in understanding the costs related to post-secondary education. Counselors go over the basics of Financial Aid and Scholarships processes. Students who are interested in playing college-level athletics will be walked through creating an account with the NCAA Eligibility Center.
Grade 12
Application Details
The session includes final details that will allow for a smooth and successful college admission process.

Senior Workshop
This half-day program held in mid-October is a check-up day for the college admission process. Seniors meet with faculty and college counselors as they complete the necessary steps which will allow them to submit their applications. Those who are still working on necessary details will have assistance in getting back on track and ready to finalize their documents. Students will be assisted in reviewing their essays and receiving needed feedback and advice; updating their Naviance account; learning how and when to request transcripts online; completing the Common Application; copying their passports, Visas, and I-20 documents that must be submitted with International student applications; practicing their interviewing skills, and fulfilling obligations required by the NCAA.
Postgraduate seminar covers a variety of topics throughout the school year in preparation for college enrollment. Some topics covered are: study skills and self-analysis of learning styles, college preparation, public speaking, and presentation skills. The public speaking and presentation skills components will call upon diverse, relevant themes including current events, ethical questions, and social decisions. All postgraduate students will be expected to serve as active participants in every aspect of the seminar.

Postgraduates participate in a special morning workshop in mid-October where counselors and faculty join together to assist them in the finer details of the admission process. Workshops include financial aid applications, individual application essay feedback, completing the common application, mock interviews, follow-up on athletic documentation and NCAA requirements, updating their Naviance account and college list, and copying documents for international students which are needed in the process.

Admission Counselor FAQ

How can I schedule a visit?
We are delighted to welcome admission representatives throughout the year. To schedule a visit, please use Counselor Community or contact our office at 203-439-7291.

Cheshire Academy hosts a yearly college fair in April. For additional information and to register please go to Counselor Community.

When using GPS please use:
50 Woodbury Court
Cheshire, Connecticut 06410 to
obtain the most accurate directions.
What other schools are close to Cheshire Academy?

Cheshire High School (1 mile)
Mark T Sheehan High School (5 miles)
Choate Rosemary Hall (7 miles)
Lyman Hall (8 miles)
Orville H. Platt (6 miles)
Francis T. Maloney (10 miles)
Southington High School (10 miles)
Hamden Hall Country Day (12 miles)

How do I get to campus?
When using GPS please use 50 Woodbury Court, Cheshire Connecticut 06410 to obtain the most accurate directions.

The College Counseling Office is located in Hurley Hall. Parking can be found throughout campus; however, designated visitor parking can be found near Bowden Hall.
What if I am running late for a college visit?
Don’t panic – please drive safely. Please contact the College Counseling Office 203-439-7291 and let us know.
What if I am missing forms?
Call the College Counseling Office at 203-439-7291. Our administrative assistant will either be able to help you or direct you to the student’s college counselor.
Can colleges send pamphlets or viewbooks to Cheshire Academy?
In an effort to be eco-friendly, the College Counseling Office is looking to cut back on hard copy information from colleges/universities. Thank you for helping us in this endeavor.
What is the best way to get in touch with a student?
We strongly suggest that you email the student (firstname.lastname@cheshireacademy.org) and cc the college counselor. Often times our international students have chosen a nickname that they prefer to use. Their email address is their given first name.
What if a student is missing test scores?
Please let us know. We can email or fax a school copy and rush them from the College Board/ACT if necessary.


Cheshire Academy has partnered with Parchment to order and send your transcript and other credentials securely. This link will open a new browser.

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