The relationship between faculty, students and families is a cornerstone of the Berkshire experience. The school takes seriously its principle of in loco parentis (“in the place of a parent”) and embodies it in many ways. Communication with families is frequent, through letters, e-mails and phone calls, and faculty and staff ensure there is always a way they can be reached.

House Heads watch over Berkshire’s boarding students and give each house a true family feeling, while Form Deans, who are in constant contact with teachers, chart the academic progress of each student. Coaches and other extracurricular leaders guide students through their afternoons, modeling teamwork and the benefits of non-academic pursuits. Working together, the school’s adults give students a sense of responsibility and productivity unique to boarding school living.

Berkshire hosts two Family Weekends each year, one in the fall and one in the spring. The Director of Parent Engagement sends regular communication to all families, and the school’s website provides families with a comprehensive view of all that is happening on campus. Berkshire's Parents Association offers opportunities for connection, volunteerism, and faculty appreciation throughout the year.
Families are also encouraged to follow daily happenings on the school’s social media outlets, including Facebook, Instagram, and Twitter.