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Why The Winchendon School?

Because a Nonstop World Needs Unstoppable Minds

Are you looking for a school that "gets you"?  Are you curious about the Admissions John Toffeyworld around you?  Are you passionate about pursuing your potential?  If you answered "yes" to any of those questions, The Winchendon School wants to meet you. We love sharing our transformative community with young adults who possess curious, unstoppable minds.

Your teachers are your allies.  If there is one thing that can dramatically propel students towards academic success, it is their relationships with their teachers. Our academic environment is designed to foster one-on-one interactions that help students discover and thrive in their learning styles.

Find your passions.  Your teachers will give you daily and weekly feedback that can frame your current and future ambitions.  Our community will provide as many opportunities as possible for you to hone in on your dreams, from theater to founding a startup, or maybe both!

Learning beyond the classroom.  Grab ahold of opportunities to study independently, travel internationally, design businesses, and launch public service programs. We'll be right there with you, building your skills and confidence to tackle anything ahead.

The process starts here.  Contact the Admissions Office for more information or, better yet, go ahead and schedule a visit and see where it leads you.

I look forward to meeting you soon.


Yours truly,


John J. Toffey VI
Director of Admissions


Why Students Love The Winchendon School

It all comes down to the people. Our students love our faculty - the coaches that support, the teachers that inspire, and the advisors who genuinely care. Each student has a team of faculty behind him or her, always ready to listen, push, encourage and inspire. The friendships made, lessons learned, and skills acquired at The Winchendon School last a lifetime.

As an exceptional boarding school in Massachusetts, our pride is in the terrific outcomes for our students: athletic scholarships, top college admissions, exciting careers, and a strong moral compass.

Open House

A world-class, innovative curriculum — custom tailored to you.

Experiential learning is at the forefront of our students’ favorite experiences, including ColLABs, Global Dynamics, and Service Learning.

Our 1:5 ratio of faculty to students creates a vibrant, passionate, and inspired community.

We work collaboratively with students to establish individual learning plans to optimize his or her experience.