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The Winchendon School

The best college prep school for students with significant unrealized potential

Academics

Jaymie Harrington

Jaymie’s background in education began when he was 18 years old and an influential coach pulled him aside to offer some words of wisdom.  Those words of wisdom and the manner in which they were delivered were life-changing and over time he realized that it became his passion to provide that message to the next generation. With two education degrees, years of NCAA head coaching experience, and experience at a jr. boarding school where he worked as an assistant dean of students and director of athletics, Jaymie looks forward to sharing his experiences and passions with the Winchendon community.  Jaymie has a wife Emilie, son Branson, and two dogs Winnie and Daisy, who are eager to join the Wapiti family.
Go-to comfort food: It’s a tie between Friends Garden and Christo’s bacon pizza!
Hero/heroine: My son, Branson.  He was born with severe hemophilia and you would never know it.  He handles his medications and doctor’s visits like a warrior and I hope I can be as tough as he is someday!
What inspires you: The opportunity to positively impact a young person’s life through my own experiences is one of the most rewarding aspects of being an educator and the main reason I find myself in the profession.  My ultimate paycheck is seeing students succeed.
What do you enjoy doing when you’re not working: I love spending time with my family in the Adirondacks, attending concerts, following all of our Boston sports teams, and finding a quiet space to wind down and relax.

Sean O’Neill

Sean joined The Winchendon School after a stint in the corporate finance world.  After some reflection, he realized that teaching and coaching will get him out of bed in the morning energized to serve his students and make an impact on their lives.  Sean combines his experiences in the working world and as a student-athlete to make his students feel prepared to pursue excellence in whatever they choose.  A former college baseball player, Sean loves to spend his free time staying active.  Whether it be hiking in the White Mountains, training in Jui-Jitsu, snowboarding, or still playing in his men’s baseball league, you can count on Sean to be up and moving.

Globetrotting adventure? Hawaii to visit my brother.

Go-to comfort food? I’d have to go with BBQ food- Brisket, ribs, pulled pork, mac n cheese, and cornbread would make up my perfect combo plate.

On the bucket list? Win a baseball championship.  That’s a major reason why I was drawn to The Winchendon School in the first place.  I had a great individual career in baseball, but I’ve always wanted to be a part of a team that wins the final game.

What inspires you? Self-improvement and trying to be a better person than I was yesterday.

Jessica Toffey

A Massachusetts native, Jessica has studied, lived, and worked in almost every region of the state. From Western Massachusetts to the North Shore and now in Winchendon where she is currently a Learning Strategist in the Hatch Center. With her deep experience in working in both public and private schools for more than ten years, she’s been teaching, coaching, and working in administration for grades k-12. She lives on campus with her husband John, children Jack, Lola, and Tobin as well as Ruffles the Goldendoodle.

What is your favorite Winch event? Any all-school event that showcases how special our kids- and faculty-are. Athletic events, plays/theatre, and especially ColLAB Symposium.

Which Winchendon class or ColLAB would you most like to take? History with Mrs. Pellegrini! She is such a dynamic educator and relates the material to current events and everyday life. She makes learning relevant and fun!

On the bucket list? Going to Spain!

Best part about being at Winch? A strong sense of community. The students are some of the best we have ever worked with; the same is said for the faculty. We really enjoy being a part of The Winch!

Elizabeth McDyer

A former Irish stepdancer from the Philadelphia suburbs, Ms. McDyer grew up coming to Massachusetts to visit with extended family so a move here to teach at The Winchendon School was a pretty easy transition. Driven by curiosity and a love of diving in to learn more (about everything), you’ll find Ms. McDyer reading, swimming, or biking when she’s not teaching.

 

Superpower of choice? Flying, to be able to visit everywhere and travel around the world!

A favorite place to visit and the books you would take there? Cape May, NJ with extended family, a fun detective novel, and the newest books recommended to me by my friends!

Go to comfort food? Peanut m&ms, butter chicken and naan, or something my mom makes!

Best part about being a teacher? Getting to know students and seeing students who think they can’t discover that they can!

Matthew Jackson

Matthew Jackson is an art historian, teaching artist, and Spanish language teacher residing in NYC. Originally from Nebraska, his affinity to cultural inquisitiveness eventually led him abroad to study art and foreign languages. He would go on to spend ten years in the Czech Republic and Spain as both a graduate student and art professional. As a teacher at an international school in Prague, he taught art history to a student body from over 50 nations. While in Spain, he worked for the Spanish Ministry of Education as a cultural ambassador in San Sebastián and a museum educator at the Museo Nacional Centro de Arte Reina Sofía in Madrid. Here in NYC, he has worked as an independent lecturer at the Museum of Modern Art and within various educative roles. Lastly, his own practice as an artist spans a variety of media and primarily engages with abstract relationships between color, pattern, structure, and form.
Matthew holds a B.A. in Graphic Design and B.A. in Spanish from the University of Iowa, a Master of Education from Colorado State University, and a Master of Contemporary Art History and Visual Culture from the Universidad Autónoma de Madrid.

Which Winchendon class or ColLAB would you most like to take?
DOCUMERICA 2022: Snapshots of Crises and Cures.
 
On the bucket list?
I’d really like to live in Baja California at some point. There’s that, or I’d also like to live in a little cottage along a stream in the Rocky Mountains.
A favorite place to visit and the books you would take there?
Italy. And I’d take “I, Claudius” and “Claudius the God” as reading material.
Hero/heroine?
My mother. She was Nebraska University’s Female Athlete of the Year as a swimmer in 1979 and one of NU’s top all-time letter winners.
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