Resources and updates for the 2023-2024 school year are available here

Why work at Cheshire Academy?

WE Put Students First

We know that each student is an individual first and a grade second. We invite you to be a part of our student-centered program where you’ll have the resources and the control over your classroom to reach each student where they are, and take them beyond where they imagined possible.

We Learn for Life

At CA, we are lifelong learners. We learn from our students every day; we read the latest journal articles in our fields; we model best practices and new practices, forming our own processes. We read together often, and share ideas in an intellectual environment.

We Teach Our Passion

Our curriculum emphasizes interdisciplinary and multi-cultural learning. We believe students should be challenged to think critically across the disciplines and imagine how knowledge might be used in our global economy. This philosophy allows for a range of exciting possibilities for your course.

we work toward Strategic Goals

Cheshire is prepared for the way education is changing in the 21st century, and we have strategic goals in place to help us grow gracefully into the changing educational landscape. Our department decisions strive to achieve the same strategic goal: provide a best-in-class, student-centered education. If this type of focused environment appeals to you, we want you to join our team!

we have A History of Inclusion

Since 1794, Cheshire Academy has practiced inclusion for our student body and faculty appointments. One of the only schools to welcome Jewish students during the second World War, Cheshire Academy was also founded as a co-educational school 226 years ago. The Academy welcomed international students as early as the 1850s, and boasted of a high Cuban population in the late 1900s during the industrial shipping era. Now, Cheshire Academy continues a tradition of inclusion by welcoming LGBTQ students and faculty with our student-led LGBTQ group and our participation in awareness programs like Day of Silence and Diversity-themed Community Weekend.

We offer a Wide Range of Benefits

Providing a work-life balance for faculty and staff is the best way to model healthy values for students. That’s why our faculty and staff enjoy a range of benefits unique to our independent school. These offerings may change from year to year depending on interest and availability.


Fitness Center


Community Gym & Pool

Breakfast, Lunch & Dinner

Opportunities for on-campus housing for teaching faculty

Generous vacation package

Intellectual Community

Faculty summer reading & discussion group

Interdisciplinary curriculum

Faculty workshops and professional development

Morton Grant for Summer Development for Teaching Faculty

Community Dinners

TIAA Retirement Options

Health, Dental, Vision and Other Insurances

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