Every year, Cheshire Academy enrolls a diverse and promising student body from countless states and over 30 countries, resulting in a truly global experience for all students, as well as faculty and staff.

We recognize that committing to an independent school education is, financially, a significant decision for families. But as an internationally minded school dedicated to individualized support and challenging its students to maximize their potential, we do not want financial constraints to limit a family from pursuing their future here.

Many students interested in attending Cheshire Academy could be eligible to apply for a variety of merit-based scholarships. Criteria and requirements for each scholarship vary.

Review the information below about each of the scholarship programs available at CA. If you need additional information, you may contact admission@cheshireacademy.org, or 203-439-7250. Additional scholarships are also available; inquire about these opportunities too.

Need-based financial aid may also be an option for families who qualify based on criteria set by School and Student Services and the CA Financial Aid Committee (See Financial Aid below).


Cheshire Town Scholarship

(for students entering 9th grade)


Originating in 1938, The Cheshire Academy Town Scholarship is open to students from the town of Cheshire applying for the 9th grade. The winner of this prestigious award receives a full, four-year scholarship to attend Cheshire Academy. Partial scholarships are offered to runner-up applicants.

For scholarship consideration, the candidate must:

  • Be a resident of Cheshire having lived in town for a minimum of one year.
  • Complete a personal interview by Feb. 1.
  • Submit a completed admission application by Feb. 1.
  • Submit, by Feb. 1, an additional 400- to 600-word essay stating why they should be our next Town Scholar. Content may include a description of interests, qualities, or unique life experiences that may set the student apart from other students. Essays can be submitted to admission@cheshireacademy.org.
  • Complete the eighth grade by June 30, 2022.

Alumni Legacy Scholarship

(for students entering grades 9-11 or postgraduate year)


This merit-based scholarship is for children, grandchildren, and relatives of Cheshire Academy alumni. If awarded, families will receive $10,000 off the total cost of a boarding tuition. This scholarship, for 5-day and 7-day boarding students, is also available to siblings of currently enrolled students entering grades 9 through 12 and postgraduate.

We take pride in the Academy’s long history of educating individual students by developing their confidence, character, and critical thinking skills, enabling them to thrive as global citizens. The Legacy Scholarship helps to ensure that this proud tradition will continue for generations to come.

Interested students who have completed their admission application by Feb. 1 and have been identified by the Admission Committee as a potential candidate for the Legacy Scholarship will be asked to further demonstrate their interest in attending Cheshire Academy by submitting a short written essay about one of the Eight Pillars of Bowden. Candidates for the scholarship will be chosen based on academic performance and demonstrated interest in a Cheshire Academy education. A family who receives a financial aid award in their first year can expect to pay a similar amount of tuition each year that their child is enrolled at Cheshire Academy, assuming their financial circumstances do not change. Eligible families may also apply for need-based financial aid.



Financial Aid


The goal of our financial aid program is to provide access to those who qualify for need-based financial aid and may not be able to otherwise afford to attend. Need-based financial aid is determined by School and Student Service for Financial Aid (SSS) and by Cheshire Academy’s Financial Aid Committee. We awarded $4.5 million in financial aid for the 2020-2021 school year, with an average award of approximately $24,500. We invite families interested in receiving need-based financial aid to apply through School and Student Services by Feb. 1. More detailed financial aid directions are available on our Tuition & Financial Aid page.