Hillside provides a warm “home away from home” for boys who live on campus either five or seven days a week. Living at Hillside offers students a wealth of possibilities for learning responsibility and cooperation. Many quickly learn that whether their housemates are from Boston or Beijing, they have much to offer each other.

Having most faculty members and administrators living on campus forms a neighborhood in which adults, skilled in interacting with young boys and in tune with their interests and concerns, are a consistent presence. All Hillside house parents are also administrators, teachers, and coaches, so boarders get the chance to know faculty members in a variety of contexts. Student leaders who have been selected as prefects and proctors also play a vital role in the houses, helping new boys acclimate to life at Hillside and serving as role models.

Selecting a boarding option (especially for a middle schooler) is an important family decision that can come with many questions and uncertainties. Hillside has carefully modeled its boarding program to be an ideal balance of structure and fun, allowing boys to gain confidence and independence in a setting that is safe, nurturing, and age-appropriate. Our house parents, and the student leaders who assist them, are trained to manage common boarding life challenges, like homesickness and roommate dynamics. Even our youngest boarders quickly acclimate to life away from home and thrive on campus, knowing that the support of a houseparent or trusted housemate is always available.