Boarding Schools Hillside School
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Hillside School is committed to providing structured, supportive, and challenging academic opportunities for young adolescent boys, both traditional learners and those with learning differences, in preparation for secondary school. Hillside’s family-oriented residential environment supports boarding and day students as they develop academically, physically, spiritually, and socially, as well as build their confidence and maturity. The boys come together from a broad range of socio-economic and racial backgrounds, and are encouraged to discover their own paths toward success.
In 1901 two sisters, Charlotte Drinkwater and Mary Drinkwater Warren, established a self-sustaining school for poor and homeless boys on their farm in Greenwich, Massachusetts. Characterized by practicality and compassion, the school reflected the sisters’ selfless desire to provide a home and basic education for young boys in need.
Today, Hillside has solidified its reputation as a premier junior boarding school providing structured, supportive, and challenging academic opportunities to a diverse population of young adolescent boys in grades 5 to 9, both traditional learners and those with learning differences, in preparation for secondary school. The Campaign for Hillside will finish in the next few years with the building of a new athletic center, the development of new center for the arts and the doubling of the school’s endowment.
Hillside’s nurturing environment provides the vital support each boy needs to learn and mature. Through our comprehensive yet flexible structure, as well as the experience that enables us to work with every boy at his own level of personal development. A Hillside boy gains the skills and confidence to challenge himself in every aspect of his life and positively broadens and enriches his character and sense of identity. He learns to look beyond himself and to recognize excellence in others, an essential step to becoming a well-balanced, productive and happy individual.
Student Leadership. There are many opportunities for students to have leadership roles at Hillside in all areas of interest (athletics, farm, chapel, technology, etc.).The student leadership program at Hillside helps students to be strong, respectful and effective leaders in their community, on the athletic field, in the classroom, in the dorm, in their place of worship and anywhere else that they may find themselves.
Chase Chapel. Originally the Hillside School wrestling barn, the Chase Chapel is the home of Hillside’s Sunday chapel services. As the weekend comes to a close, the Hillside community takes the opportunity to gather for non-denominational services at the Chase Chapel. The chapel director, assisted by students and faculty, leads chapel attendees in reflections based on the values and ethics that unite those of all religious affiliations.
Top high schools attended by students
Choate Rosemary Hall, Peddie School, Tabor Academy, Kent’s Hill, Dublin, Lawrence Academy, New Hampton School, St. Mark’s School
What the school looks for in students…