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the Cheshire Academy

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Cheshire, CT · 12

Last verified August 20, 2026

10 Main St., 64102 · (203) 439-7219

cheshireacademy.org

Enrollment

288

Student:teacher

7:1

Published tuition

$37,425–$69,400

Application fee

Auto-sourced profile. These details were collected from the school's own website and may be out of date — always confirm tuition with the admissions office. Something wrong? Suggest a fix.

Tuition by division

We don't have a grade-by-grade tuition breakdown for this school yet. The published range across all divisions is $37,425–$69,400. Most independent schools charge different rates for preschool, elementary, middle and upper school.

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Head of school

Tom Woelper

Head of School

Tom Woelper was most recently the founding head at New England Innovation Academy in Massachusetts and has worked in education, predominantly in boarding schools, at institutions such as Taft, Groton, Lawrenceville, and Hotchkiss. He will assume the Head of School role on January 1, 2025.

Curriculum & special classes

Cheshire Academy is a college preparatory boarding and day school offering a rigorous academic program balanced by a unique academic support program. It features an International Baccalaureate® Programme, the Roxbury Academic Support Program, and an Art Major program.

International Baccalaureate® Programme
Roxbury Academic Support Program
Art Major program
27 athletic teams
Theater productions

Financial aid

The financial aid program provides need-based aid, determined by Clarity and Cheshire Academy’s Financial Aid Committee. For the 2024-2025 school year, $4.5 million was awarded in financial aid, with an average award of approximately $23,750.

Before & after school care

No extended-care hours or rates on file yet. This is one of the biggest surprise costs for working parents — if you know what before- and after-care runs here, add it below.

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Admissions

The admission process for Cheshire Academy involves three main steps: Inquire, Visit, and Apply. Families first complete an inquiry form, then schedule an on-campus tour or virtual interview, and finally submit their application.

Apply by

February 1 for admission applications and financial aid applications; April 10 for enrollment decisions for accepted students.

Acceptance rate

Not listed

Application fee

Not listed

What they ask for: Inquiry form, campus tour or interview (on-campus or Zoom), application, financial aid application (if applicable) including Parents’ Financial Statement (PFS) through Clarity, and relevant supplemental tax documents.

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