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Choosing the Right Private High School for Your Child 

A well-researched decision can mean myriad opportunities for success 

Are you considering private day or boarding school for your child? You’re not alone. According to the Pew Research Center, about 10% of the country’s roughly 54.6 million K-12 students were enrolled in private school in the 2021-22 academic year. 

The reasons are many: Private schools tend to pair high academic standards and extracurricular opportunities with small class size and a sense of community and family involvement not always found at their public counterparts. 

But how do you decide which boarding or day school is a good match for your teenager? Here are a few pointers. 

Research private high schools.

Block out some time to do a deep dive into the world of boarding and day schools. Check out some of the top-rated schools in the nation to get a feel for what’s available. Since the choices are many, narrow down the list by considering family finances and how far away you feel comfortable sending your high schooler. If you’re opting for a day school, determine a mile radius and research all the schools in that area.  

Be sure to give yourself a fully rounded picture of each school – both through its website and social media presence and in national rankings and media coverage. What are the academic programs? What is the school’s reputation? Is it known for excellent athletics facilities or arts opportunities? How are extracurriculars woven into the schedule? Where do students live and share meals? Are there specialty support programs and medical facilities to assist students? 

Some schools offer signature programming that might be tailor-made for your teen. Cheshire Academy in Cheshire, CT, provides both the robust International Baccalaureate Diploma Program, the gold standard in challenging, college-prep academics, and the Roxbury Academic Support Program, which uses a theoretical framework and research-based practices to identify and work with each student’s individual learning needs.  

Make a list of the attributes of an independent school that are most important to you. 

Now that you have a good idea of what’s available, prioritize the characteristics of your ideal school. Think about your child’s needs and your family values: Do you want your student exposed to more cultural diversity? Do they thrive in a smaller class? Is building character and independence important or is the ticket to an elite college education your top priority? Is higher tuition a dealbreaker? 

In addition to a robust athletics program of 20+ interscholastic teams with a proud history of college commitments and championships, Cheshire Academy offers an Art Major and a Music Major to best prepare advanced students who plan to major in art, design, and music at the university level. Students are allowed extra time in the studio and practice space and participate in lectures and artist talks to better understand the life of a professional musician or artist. 

Reach out to the top private high schools on your list. 

If, based on proximity, price, and philosophy, you’ve been able to narrow down your choices, you may have very detailed impressions about each school on your list. Now pick up the phone! Call the admission office and ask your school-specific questions. You’ll also get a feel for how the school deals with students’ families and their comments and concerns. 

Cheshire Academy welcomes family input. The Cheshire Academy Parents & Families Association is a great way to get involved and stay connected with your student and the school. Families are encouraged to explore various volunteer opportunities and enjoy festive events held on campus, across the U.S., and internationally. You can also attend sporting events, art shows, plays, concerts, and other student activities or enjoy frequent online photo albums, videos and livestreaming.


Visit the boarding and day schools on your shortlist.  

Schedule a campus tour, information session, or interview or meet with admissions staff when they visit your area. Take a good look around and get a feel for the school culture and whether your child feels ‘at home.’  

Be sure to come prepared with questions, even those that might be answered on the website. Often an admissions professional or a student tour guide will provide off-the-cuff information or a more personal insight that gives a richer picture of campus or classroom life. 

At Cheshire Academy, all students are encouraged to be themselves, express themselves, and be open to new opportunities. Academic programs and classes are based on interest, not grade level, and taught in small groups where teachers facilitate lively discussions like a college seminar. Students take an active leadership role in their own education, developing an inquisitive nature that leads to lifelong learning. 

Virtual tour and chat options are often available. Check out the Cheshire Academy website to watch videos of students speaking about their own academic journeys, check for events in your region or schedule a one-on-one chat with an admissions counselor. CA offers a host of in-person and online sessions to acquaint you with all we have to offer. 


Armed with unique information on each school on your shortlist, your child should have an easier time expressing where he or she would like to apply. 

Review the requirements at each school. Are any essays needed? Be sure your student writes and shares those with both you and a trusted teacher or mentor to ensure clean copy and clarity.  

Gather application forms for admission, financial aid and scholarships in one place. Block out time to complete everything you’ll need before deadlines, so you don’t feel rushed. This is a big decision, but you are well prepared to give your child the opportunity to build independence, confidence and the skills needed for college and beyond. 

Good luck! 

Ready to learn more about Cheshire Academy? 

Cheshire Academy is now enrolling in select grades. Talk to an admission counselor or schedule your tour today! Contact us at admission@cheshireacademy.org or 203-439-7250. We look forward to hearing from you. 

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