On January 1, longtime educator Tom Woelper will take the reins as Cheshire Academy’s next head of school. You may know that he was the founding head at New England Innovation Academy in Massachusetts, that he’s worked at Groton, Taft, and Hotchkiss or that he was head of school at the American Pacific International School in Thailand.
But what else is there to know about the real Tom Woelper? We sat down with Tom to ask a few questions – some probing, some lighthearted – about how he approaches life, what makes him happy, and how he hopes to lead Cheshire Academy.
1. He knew Cheshire Academy was right for him through talks with the community and one key event.
What struck me from my very first visit was how everyone I met – students, faculty, staff, and trustees – shared incredible stories about CA’s transformative impact on their lives. I’m particularly drawn to CA’s philosophy of providing multiple pathways for students, whether through the Roxbury program, IB diploma, or Arts Major. The school’s commitment to meeting students where they are resonates deeply with my educational values. Plus, the global perspective here is remarkable. Cheshire Academy admitted its first international students back in the 1850s, and that’s the kind of forward-thinking legacy I’m excited to be part of. The energy I witnessed during Alexis Holmes Day and the White Out football game against Suffield Academy confirmed that CA was the right place for me.
2. He’s energized by the possibilities he envisions.
When I believe deeply in something, it becomes a driving force in my life. Right now, I’m incredibly energized by Cheshire Academy’s mission and community – I literally wake up thinking about the possibilities ahead. What really fires me up is making a meaningful difference in students’ lives, whether that’s helping someone discover their passion for history (like my high school teacher did for me), watching a student tackle a challenge they thought impossible, or seeing our graduates head off ready to shape their corner of the world. I’m motivated by that perfect intersection where belief meets impact – where what we do today creates ripples that extend far beyond our campus and far into the future.
3. Fans of a certain Scandinavian treat should try to stump him around campus.
I’ve set myself a fun challenge – learning every student’s name by the end of winter term! Here’s the deal: if you catch me around campus and I can’t remember your name, you’ll win some Swedish Fish (my road trip guilty pleasure!). I plan to get out of my office and interact with students everywhere – in the dining hall, at games, arts performances, and around campus walking my Lab, Hazel. My wife and I also plan to host students at our home, and I’ll have regular open office hours for anyone who wants to chat.
4. Rivers figure prominently in his reading.
Huckleberry Finn holds a special place in my heart – I’ve read it multiple times since high school, and each reading reveals new layers of Twain’s brilliant commentary. I’m also deeply moved by Norman Maclean’s A River Runs Through It – it’s a beautiful meditation on family, nature, and the art of fly fishing in the Montana wilderness. Maclean’s line about being “haunted by waters” captures something profound about how our past shapes us. And I’m a devoted reader of The Atlantic – it helps me stay engaged with current issues and different perspectives, which often leads to fascinating discussions with students and colleagues about everything from technology and culture to global affairs.
5. Is he a history buff? You bet.
History captured my imagination, thanks to an incredible teacher who was also my dorm parent when I was a student at Lawrenceville School. His passion for Lincoln was contagious – so much so that I not only majored in history at Princeton but wrote my senior thesis on Lincoln’s 1864 reelection! That early spark led me to some of my favorite historical works: James McPherson’s Battle Cry of Freedom, which brings the Civil War era to vivid life (and which he wrote when I was a student at Princeton), and Gordon Wood’s, Radicalism of the American Revolution, which I read in graduate school and transformed my understanding of how revolutionary that period truly was. Looking back, it’s amazing how one great teacher shaped not just my college path but my whole career in education.
6. Like many Cheshire students, he’s always “present.”
For me, it all comes down to wellness habits and being truly present in whatever I’m doing. I’m a big believer in routine – getting good sleep, eating well, and making time for exercise. When life gets busy (and in schools, it always does!), these habits become even more crucial, though they’re often the first things we’re tempted to drop. I’ve learned that being fully present matters tremendously – whether having dinner with my wife, walking Hazel around campus, or meeting with students. When I’m working, I’m fully focused on work; when I’m home, I’m fully home. It’s not always perfect, but this approach helps me maintain balance and manage stress in a demanding but rewarding role.
7. His labrador retriever Hazel approves of his favorite workouts.
You’ll often spot me around campus walking Hazel, my Labrador retriever! I’m an enthusiastic squash player, and I balance that with yoga and Pilates. My wife and I (and Hazel) are avid hikers – there’s nothing better than losing yourself on a trail and getting your heart rate up while connecting with nature (once I get settled, I’d love to hear recommendations for the best hiking spots near Cheshire!).
8. You’ll find him in the cookbook section of any bookstore.
I’m on a mission to expand my cooking skills! While I’ve always been the family grill master, COVID turned me into the breakfast chef, too. Now, armed with the NYT cooking app and coached by my patient wife, I’m venturing beyond scrambled eggs and pancakes.
9. An unexpected day off might find him hitting the beach – or the hills.
You’d likely find me hiking with my wife and Hazel, though if it’s beach weather, I might swap the forest for sand between my toes and the smell of salt air. I also love discovering local coffee shops – finding that perfect spot where I can settle in with a good book and a great cup of coffee. One of my first missions in Cheshire will be finding my go-to café.
10. An African safari would fit his travel plans well.
I’ve been incredibly fortunate to explore places from Tibet to Antarctica, New Zealand to Burma. My love for travel started in college when I led bike tours through Europe. The only continent I haven’t visited is Africa, so a safari adventure is definitely on my bucket list!
BONUS: He’s no shrinking violet when it comes to belting out a favorite tune.
While I regret not learning guitar when I was younger (it’s never too late, right?), I’m not shy about singing – whether in the car, around a campfire, or even at karaoke nights!
Want to know more?
It’s clear Tom Woelper will make his mark at Cheshire Academy, striking a delicate balance between preserving what makes the school special and setting new goals for a bright future. He addressed some other faves and philosophies during a walk around Bowden Hall. Watch it below!
