Step Up. Take Advantage of Everything.
Community is core to our school. Research shows us you’ll learn faster and better when you have strong connections to those around you. You’ll find opportunities built into your day to make connections or, if you’re on our Massachusetts campus, you’ll find day and boarding students mingled all across campus- gaming in the dorms, getting ready for a dance, or cheering each other on when the volleyball team reaches the championship round.
Advisory Program
Once you arrive at The Winchendon School, you’ll be signed an advisor. Your advisor will meet with you in your small group of 6 to 8 students of varied backgrounds and in one on one sessions. Your advisor is there to help you map out your weekly commitments, help you stay on track in your classes, work through concerns you have, and in general, be in your corner at all times.
Wellness and Fitness

Under the direction of the Assistant Head of School, you’ll learn important life skills (and we don’t just mean doing your laundry), gain confidence, and learn how to navigate relationships outside of your family before heading off to college.
Our Health Center is staffed for immediate medical attention, counseling, health education, and resources that are available to students, faculty, and staff.
The local hospital is ten minutes away if needed.
Sunday Brunch. Team Lifts. A Coffee House.
Residential Life at The Winchendon School Will Surprise You.
Each dorm is supervised by dorm faculty and well as student proctors who provide day-to-day care and supervision of our residential community. Walk into any dorm room and you’ll find yourself surrounded by friends, listening to music, doing homework, practicing their lines for the play, or playing knee-hockey.
Day students are encouraged to hang out on campus, eat breakfast with their team before all-school meetings, or hang out with friends over dinner – you’ll find day students do everything our boarders do except move in!
Several weekends a year the Massachusetts campus has closed weekends. All boarders stay on campus, day students join them and everyone participates in activities together.
The Best Thing About Living on Campus?
Your roommate just may be your best friend for life.


Our Winchendon Speaker Series brings three to four speakers on campus every year including Travis Roy, Sam Drazin, and Brooklyn Rainey to name a few.

Weekend Activities
On Monday during morning all-school meeting, you’ll be presented with a dozen possibilities for the coming weekend. Past activities have included:
- Movie-mall Trips
- Dinner out in Worcester
- Paint Ball Trips
- Roller Kingdom
- Night Skiing
- Canoeing
- Sushi trips
- Coffee House on Campus
- Snow tubing
- On-campus basketball tournaments 5 v 5 and 3 v 3
- Dances | Prom
- Student Productions

Where to Next?
We suggest checking out these pages: