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What If There Was a Way to Be Sure Your Teen's Next School Is The Right Fit?

Now There Is. 

Is buying a house easier than choosing a private high school for your teen? Not with our six-week happiness trial. We believe so firmly that your teen will be happier at The Winchendon School that we'll refund your unused tuition if they're not. We call it #TheWinchWay.


Brooklyn, NY

Winchendon’s NYC campus is purposefully located in the center of Brooklyn, in a building owned by the CDSC, a long-time provider of services for the BedStuy, Clinton Hill and Fort Greene neighborhoods.  Students can be tackling quadratic equations or the next draft of an essay one period, and 10 minutes later, moving downstairs to help in the food pantry or the hydroponic garden. With a subway stop less than 200’ from our door, commuting and access to all of NYC is easy.

Want to learn more about seeing your teen be happy in school? We're here to help you discover The Winchendon School.

"We are thrilled to see her with confidence and motivation for her school work, which we attribute to the support and encouragement of the staff, and to the value that Winchendon places on the learning and well-being of each student."
Parent. '22

CDSC Scholar award winner tending garden.

Increased Opportunities For Every Student

Study What Makes You Curious

Study the American Revolution in the heart of Massachusetts or street art in New York City, at The Winchendon School we see education as active not passive. Our classes are engaged where students lead discussions, debate questions, and draw their own conclusions.

See our full range of courses. Review our Curriculum Guide.

Unlimited Electives

Each year every student has the opportunity to take an idea and design an internship or independent study during ColLAB. 

Your elective choices are only limited by your curiosity.

Meet Our Leadership Team

Sean Duncan
Head of School

Blessed with an abundance of energy and ideas, Sean directs curriculum innovation at The Winchendon School. This has included, in recent years, the ongoing evolution of Global Dynamics and ColLABs among other important initiatives. After sojourns at Gould Academy and in finance, Sean first came to Winchendon in 2008 and then returned in 2012 after a very brief time away working in an urban charter school. He is duly proud of the evolution of the ColLAB Program and its symposium finale. “It’s just awesome to see the students take so much pride in their projects and celebrate one another’s learning. We talk a lot about how we can empower our students to become more confident and creative people, and this event is a superb platform that puts student growth in these areas on display.”


Gladys Gross

Gladys joins us from Kildonan, a school renowned for its work with students with learning differences, and has taught everything from middle school language arts through AP Literature and Composition, as well as Spanish at all levels. Gladys will be our lead Learning Advocate and Spanish teacher. She has tremendous school experience, having taught in Berlin and as a founding faculty member of Islands High School in Savannah, Georgia.

Magee-1 (1)

Jared Magee

Part of Winchendon’s small, but proud, southern contingent, Jared’s many faceted interests are reflected both in and out of his classrooms and extra-curricular activities. This self-described “ pragmatic dreamer, a dreamy pragmatist, a poet, a musician (three released albums), and a student of life” has an explorative streak. Towards his goal of touching down on all seven continents he has scored four of them – Africa, South America, and Antarctica remain…maybe there is a ColLAB to be devised with those destinations in mind!

Video Series

Living and Learning on the Long Trail

Your Curiosity Defines How Far You'll Go 

Conference Period: How We Use It