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The tone of Hampshire Country School is set by its large faculty of classroom teachers, dorm parents, and activity instructors. Altogether, there are about two full time faculty members for every three students. Most full time faculty members live on campus, eat many of their meals with students in the school dining room, and participate in informal activities and special events on weekends and holidays as well as school days.

Of the 18 full and part-time faculty members, about six are academic faculty, six are residential life staff, and six are involved with students in more general ways, including administrative and supervisory roles. Part-time faculty (who do not live on campus) include a music teacher, a skiing instructor, and a nurse.

Faculty members are chosen not only for their academic training and teaching ability, but also for their ability to be good role models for students, their liking for the kinds of students who attend Hampshire Country School, and for personal qualities such as integrity and reliability.

Teachers and other faculty are selected especially for their ability to appreciate, challenge, and stimulate students with high scholastic potential. It is important that they be able to work with educational and personal deficiencies in their students; but the success and fulfillment which most Hampshire Country school students achieve results primarily from stimulating their interests and abilities, not from focusing on their deficiencies.