Hillside 101

Founded in 1901 by sisters Charlotte and Mary Drinkwater in Greenwich, MA.
Relocated to its present location in Marlborough, MA in 1927.
Ed Chase was appointed Hillside’s tenth headmaster in October, 2015.

Facilities and Grounds
150 acres of land
Full working farm and greenhouse
Six dormitories, and housing for faculty and staff.

Class size: 8-12
Student to faculty ratio is 7:1
Foreign languages offered: Mandarin, French, Spanish.

40 faculty members
In addition to working in the classroom, faculty members serve as coaches, dorm parents, advisors, role models and mentors.

Tutorial Support
Class size: 2-4 students
Tutorials taught by certified learning specialists are offered in: Language Arts, Math, Social Skills, and Organization.

Secondary School Placement
Recent graduates have gone on to schools such as Phillips Andover, Phillips Exeter, St. Paul's, Choate, Williston, Berkshire, Winchendon, Dublin, Lawrence Academy, New Hampton School, Kimball Union Academy, and St. Mark’s.

First Round Applications due January 31st. Applications accepted throughout the year depending on space and availability.


165 Students
65% Boarding / 35% Day
14 states and 12 foreign countries represented

  • 7 – Day Boarding $57,400
  • 7 – Day Boarding (International) $60,700
  • 5 – Day Boarding $50,800
  • Day Student $33,600
* other mandatory fees not included

20 activities/athletics during the year including soccer, basketball, tennis, lacrosse, baseball, drama and band.
The New England Sports Center serves as our home ice for our hockey program.

Core Values
Compassion, Determination, Honesty, Respect, Fun

Hillside is proud to be a member of these leading independent school organizations:

NAIS Proud Member

Association of Independent Schools of New England

TABS Proud Member