Resources and updates for the 2024-2025 school year are available here

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Cheshire Academy offers a wealth of academic resources dedicated to helping every student succeed as a global thinker, whether through our accessible library database; a writing center committed to cultivating confident, creative writers; a math lab staffed each day by department faculty; advisors devoted to guiding students through school and teenage life; courses set to helping students flourish on the SAT and ACT; extra help periods built in to the school day; or classes designed to welcome and support diversity on our campus.


The mission of Cheshire Academy’s Center for Writing is to cultivate confident writers who enjoy writing as an integral aspect of their everyday life. We believe confidence is generated in an atmosphere of collaboration where emphasis is placed on the writing process. The Center strives to help students find joy in writing. The writing center serves all members of the community in every phase of their writing including: idea generation, organization, development, and editing. We focus on supporting writers in all genres including research, academic, creative and informal texts.

Educational Services FAQ

To meet the needs of a wide range of learners, including those with learning disabilities or other exceptionalities, Cheshire Academy provides accommodations in accordance with the Americans with Disabilities Act (ADA).

How can a student receive accommodations at Cheshire Academy?

To receive accommodations, documentation must be provided from a qualified learning specialist, psychologist, or medical provider that indicates a physical or mental disability that substantially limits a major life function such as concentration, learning, or health-related impairments.

The documentation should be current, typically within the past three years, in describing the impact of the disability on student learning and should demonstrate a link between functional limitations and requested accommodations.

Does Cheshire Academy provide testing for learning disabilities or ADHD?

Cheshire Academy does not conduct formal evaluations or testing for the identification or reevaluation of learning disabilities, ADHD, or other exceptionalities. The director of the Roxbury Academic Support Program can provide more information as well as a list of private evaluators.

How does the accommodations process work at Cheshire Academy?

Learning accommodation plans are developed for eligible students and reviewed with teachers, advisors, students, and families by the director of the Roxbury Academic Support Program. Accommodations for each student that can be provided by Cheshire Academy are determined based on their unique profile of strengths and areas of challenge.

How can a student receive accommodations on the PSAT, SAT, or ACT?

Cheshire Academy facilitates the application for accommodations on the PSAT, SAT, or ACT for eligible students. More specific information regarding documentation guidelines for standardized testing is detailed by ACT and College Board. The director of the Roxbury Academic Support Program contacts families for permission to apply for accommodations, advises students and their families of the various deadlines and options for each type of test, and obtains documentation from families as needed to support the requested accommodations.

A student has an Individualized Education Plan (IEP) at their public school. Will they have an IEP at Cheshire Academy?

Cheshire Academy does not provide special education services or implement goals and objectives on IEPs. However, a personalized and collaborative approach to designing a students’ academic plan, reasonable accommodations, academic advising, designated extra help blocks, writing lab, math lab, and supplemental academic coaching support a range of learning needs. We work to help all our students develop skills and strategies necessary for success at Cheshire Academy and beyond.

Advisory Program

All students are assigned to grade-level advising groups led by faculty advisors.

Each week during the advisory period, advisors lead their groups in discussions about school expectations and timely issues of importance to the entire school community. This time is also used for group reflection and team-building activities. Groups and advisors remain consistent from year to year.

On an individual level, an advisor helps a student explore their interests and maximize their potential. They facilitate short-term and long-term goal setting, help students process feedback, and guide students in reflection on their progress. Advisors help students navigate both expectations and opportunities at the Academy and remain in communication with the teachers, coaches, dorm parents, college counselors, and other faculty members who support each student.

Advisors serve as advocates for their advisees and the initial point of contact for parents/guardians. Advisors communicate regularly throughout the year with parents/guardians to keep them informed and maintain a partnership in support of each student. Parents/guardians are encouraged to reach out to a student’s advisor any time a question or concern arises. Questions or concerns regarding a student’s advisor should be directed to the Academic or Community Life Office.

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