[7] Berkshire’s academic year is divided into trimesters with a week-long winter session.

In addition to tuition, 2/3 of Berkshire parents also contribute to the annual fund, which typically nets almost $3 million each year.

[11] Whilst Unsworth incorporated drug-awareness and counseling programs[11] after a series of drug-related incidents he resigned his post.

[4] The board of trustees turned to Paul Christopher (1996 - 2002), an ethicist and previous head of philosophy at West Point, New York,[4] as the next headmaster to address the renewed public embarrassment around drugs.

[4] In June 2002 Christopher resigned as headmaster "amidst sexual harassment allegations.

The Stewart Athletic Center was named after Jackman Stewart, a longtime Berkshire athletic director who also, at times, served as the school’s dean of students, dean of admissions, and director of development.

The Stewart Center features two ice hockey rinks (one Olympic size and one NHL Regulation size), as well as 14 locker rooms, a full athletic training suite, a fitness center, and various conference rooms and offices.

The Athletic Center also hosts campus events such as choral festivals and the school's commencement.

Between 2021 and 2023, 100 Berkshire graduating seniors signed to play sports at the collegiate level.