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


A staple of the independent school experience at Cheshire Academy is our advisory program. Students are assigned to small groups that are led by faculty advisors who help guide students through their years at the Academy. Formal meetings happen once a week, but most students see their advisors daily, sometimes just for a quick hello in the dining hall, passing between classes, or in the dorms. During advisory meetings and one-on-one conferences, advisors discuss academics, athletics, character education, topics important to the school community, and other issues relating to school and social life.

Topics during advisory meetings include:

  • management and organization skills
  • study skills
  • academic integrity
  • team-building and relationship-building
  • community responsibility
  • diversity, equity, and inclusion
  • responsible use of technology
  • stress relief and social-emotional learning
  • and culture and traditions

Advisors are there to support their students when they need it by serving as mentors and advocates. Advisors are an active part of student life, keeping track of academic performance, athletic and artistic endeavors, and general well-being. Sometimes, advisors provide guidance and then step back and watch the students learn and succeed on their own, while still checking in regularly. Other times, advisors take a more hands-on approach, giving more personal attention and structured support to the students who need and want it. The flexibility in this working relationship is part of the student-centered experience, giving students the support they need, when they need it.

Advisors also act as an important link between families and the Academy. Regular contact helps families stay involved in their child’s academic and social development throughout the school year. This can be particularly helpful for boarding and international student families who live apart from their children.

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