Hillside School

  • Founded: 1901
  • Address: 404 Robin Hill Street - Massachusetts, United States (Map)
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Since its founding, Hillside School has committed to offering the best educational experience in a structured, supportive environment. Our boarding and day program for boys in grades four through nine is unique in its ability to meet each student at his learning threshold and then truly maximize his potential. Hillside parents frequently give us credit for providing what is a transformative experience for their sons.

Hillside School was founded in 1901, when two sisters established a self-sustaining school for boys. Practicality and compassion drove the genesis, along with a commitment to providing a structured, supportive, and challenging academic environment. Hillside’s diverse offerings and character education have contributed to the development of superbly well-rounded young men for over a century. Hillside students, then and now, are encouraged to take risks with the knowledge that sometimes they will fail, but the support of their school community will never waver. Basic tenets such as determination, compassion, and tolerance guided Hillside students in 1901, just as they do today. The relevance of Hillside’s founding principles remains, and these values continue to shape the school community.

Today, Hillside is a premier junior boarding school providing exceptional academic opportunities to a diverse population of young adolescent boys in grades four through nine in preparation for secondary school. The school is defined by its culture of inclusivity that fosters close relationships between students and teachers, made possible by a 4:1 student teacher ratio. Students are encouraged to push themselves academically while constantly focusing on the school’s core values of compassion, determination, honesty, respect, and brotherhood.

A successful Hillside graduate evolves from a student who strives for academic triumph and gives his all to his teammates into a man who becomes a valuable member of his community, a worthy colleague and friend, and—someday, perhaps—a dedicated husband and father. A Hillside boy knows that achievement gained at the expense of another is empty, while one born from collaboration is a reason to celebrate.

This will be achieved through our small class size, 4:1 student teacher ratio, and our academic support programs tailored to meet each boy's needs. Our extra curricular programs will develop and challenge each student to perform at his highest level through practice, competition, and outstanding teacher support. Spiritually, the school’s focus on others, empathy, brotherhood, and leadership will develop the soul and spirit of each student.

Standards and expectations are the guideposts for success at Hillside School. Our boys learn to embrace the school’s core values of compassion, determination, honesty, respect and brotherhood throughout their Hillside careers and beyond. By living these values, Hillside students prepare themselves for lives of meaning and purpose.

Our boys’ efforts in achieving the Hillside core values are measured through our Shades of Blue system. This communication system monitors student progress and behavior, brings attention to areas of concern, and often prevents small issues from escalating. Shades of Blue is also essential to Hillside’s effort to keep parents informed of their son’s academic and behavioral success and areas of challenge.

Students who model and even exceed the Shades of Blue standards are recognized by our Bulldog of the Week and Bulldog of the Term awards, which further emphasize the central importance of our core values. Thanks to the patience, guidance, and dedication of our caring community, all of our students have the ability to reach the highest levels of Shades of Blue and, in doing so, realize their full potential as students and individuals.

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Community Reviews (2)

The exceptional guidance from the staff has not only enhanced my child's love for learning but also propelled their academic growth to new heights.
By D.L. (Jan, 2024) |

My child has thrived at Hillside School. The quality of education provided is outstanding. The staff is incredibly helpful and supportive, ensuring that every student's needs are met. I have seen tremendous progress in my child's academic and personal growth. Hillside School has truly exceeded my expectations.
By Layla (May, 2023) |