Overview
The KMS community is divided into six houses with members brought together from all of the different teams and groups in the school. The director of student activities provides several events over the course of the year to get together and compete for house points in competitions ranging from pumpkin-carving to dodgeball. The year culminates with the award of the Hasse Halley Community Cup. Community House events are published on the KMS Community Calendar, found on main page of KMS website.

Hasse Halley Cup
This competition honors Dr. Hasse Halley, who was the head of the English Department and the director of academics at Killington Mountain School when she passed away. In her memory, KMS established the Hasse Halley Cup, which brings together student-athletes, staff and faculty in six community groups. Each group is known as a House and made up of student-athletes from various disciplines as well as staff and faculty, and the six houses compete throughout the year for "Master Points," which are awarded in a variety of good-natured contests, from chess tournaments to dodgeball games. The variety of contests allow student-athletes and staff alike to reveal hidden talents, from a math teacher's unexpected prowess at dodgeball to a student's ability to craft an unexpected haiku during a poetry contest. At the senior awards and recognition ceremony each April, the team that has amassed the greatest point total throughout the year is recognized and awarded the Hasse Halley Cup.