[2] The school was the first in the United States to host a yearly Boar's Head & Yule Log pageant.

Most teachers have roles in addition to teaching at the school (sports coach, dorm parent, etc.)

Despite the school's sectarian status, students belong to a variety of faith backgrounds or are irreligious.

Breakfast is served in the morning of every school day, including Saturdays, after which students are required to go to a chapel service, before classes.

Below the dining hall is the "Squeelery", a rec room with table tennis, foosball, and a small shop selling snacks.

Sports facilities include a large multipurpose grassy field area, tennis courts, and the Harry Dickie Sports Complex gymnasium with a full-sized basketball court, fitness center, weight room, and indoor swimming pool.

Near the school's entrance is a large pond which has been used in the past for kayaking and canoeing in warmer weather, and is still used for impromptu recreational hockey and ice skating in winter.

In deference to the steadily increasing female student population, a women's hockey team was formed at the start of the 2016-17 season.

[15] Hoosac now competes in AAA basketball, the highest level of competition for prep schools.

Other sports offered include soccer, lacrosse, basketball, golf, volleyball, skiing, cross country, and flag football.

During the winter trimester only, the school also has skiing, which involves daily trips to Jiminy Peak.

A private ski slope with a tow rope[16] is open to the entire student body on weekends.