Town Scholarship
The Town Scholarship is one of the many ways we honor and support our relationship with the residents of Cheshire, and it has a long and proud tradition. Originally established in 1937, more than 87 Cheshire residents, including James Van Der Beek '95, have received the scholarship.

The selected candidate receives a full four-year scholarship to attend Cheshire Academy as a day student. Three runner-up candidates receive partial four-year scholarships. Selection for the award is based on scholarship, citizenship, leadership, and the potential to contribute positively both to the Academy and the greater community.

To Qualify:
  • Candidates must be residents of Cheshire, Connecticut, who have lived in the town for a minimum of one year
  • Candidates must complete the eighth grade by June 30, 2017
  • Submit all scholarship application requirements by their required dates

Scholarship Application Requirements

  1. Fill out your detailed inquiry form, after which you will receive application instructions via email
  2. Take the Secondary School Admission Test (SSAT) before January 1. Please visit for details or contact us for the dates we will offer the test on campus
  3. Schedule or complete a personal interview by December 20
  4. Submit a completed application by January 20
  5. Submit the required Town Scholarship essay by January 20 A 400-600 word essay describing why you should be our next Cheshire Town Scholar describing your interests, unique qualities, or anything else that sets you apart from other students
Finalists will be called back for a panel interview in early February. The Town Scholar will be chosen and notified by March 10.

Questions? Email

The deadline for the fall of 2017 has passed. If you're interested in future years, let us know by filling out the form below.


Cheshire Academy
10 Main Street
Cheshire, Connecticut 06410

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

About Cheshire Academy

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  • The student-centered private school in CT

    Cheshire Academy is a boarding school in Connecticut that challenges students in grades 9-12 and Post Grad to discover and hone their unique talents. This college preparatory school offers personalized learning opportunities like the Roxbury Academic Support Program and the IB Program. Artists can benefit from the Art Major program, while high school athletes can benefit from competitive athletics. Overall, students at the private school are encouraged to become culturally sensitive and internationally minded, and develop the critical thinking skills, confidence, and character that enable them to succeed in college and as citizens of a global society. 
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