History of Cheshire Academy in Timeline

By Popular Timelines Editorial Team · Updated: May 6, 2025

Cheshire Academy, located in Cheshire, Connecticut, is a co-educational college preparatory school. Founded in 1794, it is the eleventh oldest boarding school in the United States. Formerly known as The Roxbury School, it initially focused on preparing young men for Yale University. Cheshire Academy is notable for being the first private academic institution to accept international students, beginning in the 1850s. Furthermore, as of 2011, it was the only independent school in Connecticut to offer the International Baccalaureate Diploma Programme.

1917: The Roxbury School

In 1917, the Episcopal Academy was known as The Roxbury School.

1917: School Purchased by Roxbury Training Center

In 1917, the school was purchased by the Roxbury Training Center, and was no longer open to both men and women. The Roxbury School focused on training young men to enter Yale University and focused on rigorous academic preparation.

1917: School Renamed The Roxbury School

In 1917, the school was renamed The Roxbury School, and exclusively trained young men to attend Yale University.

1937: Cheshire Academy

In 1937, The Roxbury School was known as Cheshire Academy.

1937: Town Scholar Program Established

In 1937, the Town Scholar Program was established, providing a full, four-year scholarship to a resident of Cheshire entering the ninth grade.

1937: School Became Cheshire Academy

In 1937, under headmaster Arthur Sheriff, the school became Cheshire Academy.

1969: School Returned to Co-ed Beginnings

In 1969, the school returned to its co-ed beginnings, allowing both young men and women to attend classes together.

2011: Only Independent School to Offer International Baccalaureate Diploma Programme in Connecticut

As of 2011, Cheshire Academy is the only independent school in Connecticut to offer the International Baccalaureate Diploma Programme.

2011: Cheshire Academy began to offer the International Baccalaureate Diploma Programme

In 2011, Cheshire Academy began to offer the International Baccalaureate Diploma Programme during the 2011-2012 academic year.

2011: Dedication of Simosa Track and Field

In the fall of 2011, Cheshire Academy saw the dedication of the new Simosa track and field.

2012: Cheshire Academy began to offer the International Baccalaureate Diploma Programme

In 2012, Cheshire Academy began to offer the International Baccalaureate Diploma Programme during the 2011-2012 academic year.

2022: Construction of New Tennis Courts and Playing Fields

Over the summer before the 2022-2023 school year, Cheshire Academy constructed new tennis courts and playing fields on their campus.

2023: Simosa Track and Field Updated

Over the summer before the 2022-2023 school year, the Simosa track and field was updated at Cheshire Academy.

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