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The Winchendon School

The best college prep school for students with significant unrealized potential

Learning Strategists

Kara Santoro

Kara Describes herself as “teaching enthusiastically and using the knowledge she gained from previous coaches to keep a positive and competitive family culture for her teams.” When off duty, Kara enjoys playing roller hockey and deck hockey or will find herself indulged in the Marvel Cinematic Universe.

Favorite Place and Book: My favorite place is Lake George, NY. I travel there every year with my family and many of our family friends. Every year we find something new to do and explore, but we always make sure to leave a lake day or two for boating and lounging. A book that I found myself reading there is Relentless by Tim Grover. The book speaks to competitive athletes and how they do what they do. Many of the lessons described can be translated off the ice and implemented into a person’s mindset for life.
Bucket List: My major bucket list item is to skydive in all 50 states. I love to travel and I would love to see all of the USA – what better way to do it than 10,000 feet in the air! My first jump was actually in 2020 in Saratoga, NY during our annual trip to Lake George.

Go-to Comfort food: My go-to comfort food is hands down Chipotle.

Superpower of Choice: I always love this question because there are so many possibilities and weighing the pros and cons of each could take a lifetime. But, I think I would have to go with teleporting. The thought of not having to fly on a plane or drive for hours (or days) is incredible. It would also make getting to all 50 states to skydive a lot easier!

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!

Phil Simplicio

Phil is passionate about helping others and getting the best out of someone. He is an avid Boston sports fan, a UCONN basketball fan, and a Notre Dame football fan. As a teacher, he is excited to be at Winchendon. At Bates College, he majored in Economics with a minor in Religious studies and a concentration in Education. He was also a leader on the Bates football team, and loves golf, cribbage, and reading.

A favorite place to visit and the books you would take there? My favorite place in the world is Popponesset Cape Cod. I would bring my biographies on Bill Belicheck and Willie Mays and sit right by the ocean with my toes in the sand. 

On the bucket list?  Get to a game at Notre Dame stadium. 

Hero/heroine? My Grandpa, Richard Roche. He is the best man I know.  

Song to start the day? That’s Alright by Just Like Us 

Bernard Lipat

Bernard Lipat

This past spring, Bernard completed his Ph.D. in Applied Physics and Applied Mathematics with a concentration in Atmospheric Science at Columbia University in the City of New York and at NASA/GISS as a NASA Earth and Space Science Fellow. His dissertation was entitled “Quantifying the Linkages between Clouds and the General Circulation of the Atmosphere”. At Columbia University, Bernard served as co-chair of the department social committee and co-founded qSTEM — the organization for queer graduate students in STEM. Before that, Bernard completed his undergraduate degree from New Jersey City University with a double major in Mathematics and Psychology as well as a minor in Computer Science. There, he served as President of the Psychology Society, President of the Math Club, and President of KME — the mathematics honor society.

Globetrotting adventure: Brasil!

Go-to comfort food: Mac & Cheese

Favorite place and books on hand: Any play by Ibsen, read while cuddling my dog

Song to start the day: I feel better – Hot Chip

Superpower of choice: Telekinesis

Madeline Legro

Maddie moved to New York in 2016 after receiving her Bachelor of Arts in Ethnomusicology and Classical Studies from Bates College. Since then, she’s worked full-time as an audio engineer and part-time as a barista, bookworm, and folk musician. Maddie is thrilled to be an incoming faculty member at TWS Brooklyn!

Which Winchendon class would you most like to take: I’d most like to take “The Sword, Pen, and Arrow: Freedom is Born out of Function” ColLAB!

Superpower of choice: Shapeshifting!

What you’re looking forward to the most this year: I’m most looking forward to learning and growing with Winchendon Students, designing ColLABs, and diving deeper into social justice in Brooklyn.

On the bucket list: See the Aurora Borealis, travel to Timbuktu by Jeep, record a studio album.

Claire Parker

A recent transplant from Texas, Ms. Parker enjoys show tunes, trying new food, and a good ghost story. She and her dog Pocket have settled into life on campus.

Superpower of Choice: Shapeshifting

Go to comfort food: Cheesecake

Favorite book: The Girl with All the Gifts by M.R. Carey

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