The College Counseling Office

The college counseling office supports students at every step of the college application process, from discovering strengths to overcoming weaknesses, registering for standardized tests (SAT, ACT, and/or TOEFL), meeting with college representatives, visiting college campuses, writing application essays, completing applications, and submitting transcripts and recommendations to selected colleges. We ensure each student’s college process to be a rewarding and positive experience.

College Counseling at Cheshire Academy

List of 5 items.

  • 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.

    During our seminars we expose students to college applications, essays and their meaning in the process, resume building, the personal characteristics sought by colleges when they review applications, the importance of involvement in the school community, and the details of accurately completing the college application and submitting it on time. Part of every seminar includes thoughtful discussion about the process and life after Cheshire Academy.
  • College Counselor Relationships

    As counselors, we attend regional and national conferences on the admission process, present sessions at professional meetings, engage in our own campus visits, and build strong relationships with admission officers. Our counselor letters of recommendation provide positive communications with colleges which highlight student’s education, activities, contribution to school life, and potential for making a difference at the college of their choosing.

    We assign sophomores to college counselors in January and meet both individually and in small group sessions through the year. After we have completed our first meeting with sophomores we invite parents to meet with us in April or May to add their perspective to the process. Our roles are multifaceted. 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

    Each year Cheshire Academy hosts over 100 college representatives in the fall who meet with students; we also sponsor a spring college fair on campus for sophomores and juniors that draws more than 150 college representatives from around the world. Cheshire Academy juniors meet one-on-one with a representative from a college for a mock interview.
  • Parent Involvement

    We involve parents in every part of the process and invite them to our junior College Day program, the college fair, and our bi-annual athletic recruiting program. 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.
  • Senior College Workshop

    Seniors 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.

The College Process

List of 5 items.

  • Freshmen

    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.
  • Sophomores

    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 admissions 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.
  • Juniors

    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.

    The College Admissions Process, an in-depth review. This session covers the components of the college admissions 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 a and additional resources for advice and expertise are cited and discussed.
  • Seniors

    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.
  • Postgraduates

    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. 

College Counseling Office

List of 3 members.

  • Madeleine Bergstrom 

    Director of College Counseling
    Phone: 203-439-7550
    Keene State College - BA
    Bay Path University - MS
    Univ. of California - San Diego - Certificate
  • Laura Dempsey 

    Senior Associate Director of College Counseling
    Phone: 203-439-7294
    Univ. of North Carolina, Greensboro - BS
  • Sarah Lasoff 

    Associate Director of College Counseling
    Phone: 203-439-7552
    Cabrini College - MS
    Immaculata University - BA


Cheshire Academy
10 Main Street
Cheshire, Connecticut 06410

MAIN PHONE: 203-272-5396
MAIN FAX: 203-250-7209
ADMISSION OFFICE: 203-439-7250
ADMISSION FAX: 203-439-7601
ATHLETICS OFFICE: 203-439-7242 

About Cheshire Academy

List of 1 items.

  • The Student-Centered Private School in Connecticut.

    We put the unique needs of every student first. That’s why we offer 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 can stretch their intellectual boundaries by taking one of 20 advanced International Baccalaureate® Diploma Programme courses, or practice new skills by participating in a range of afternoon programs including; athletics, fine arts, and performing arts. We are also the only Connecticut private school to offer one-on-one student coaching through our Roxbury Academic Support Program.
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