The Foundation for a Meaningful Life
Kindergarten - Grade 9 in Southborough, MA
Fay Magazine: Summer 2025

Faculty Profiles: Trey and Shannon Dugger

Meet music teacher Trey Dugger and Director of Counseling Services Shannon Dugger, and learn what life is like raising a family on campus.
Trey and Shannon Dugger arrived at Fay in 2016, drawn by the close-knit community of young families. Trey joined the Arts Department as a music teacher, teaching Music Exploration, Beginning Band, Concert Band, Wind Ensemble, String Orchestra, and Jazz Band, in addition to launching Fay’s first studio recording class. Meanwhile, Shannon spent several years working as a school counselor in area schools and as the assistant principal at Potter Road Elementary in Framingham, Massachusetts. She joined the Fay faculty full-time in 2023 and serves as Fay’s Director of Counseling Services. Together, Trey and Shannon also serve as dorm parents to the Village Boys dorm. We sat down with Trey and Shannon this spring to talk about raising their children, Aidan ’19, Jazz ’31, and Ella ’33, on campus, the special privilege of having Fay’s seventh grade boarders in their care, and how all the different ways that they work with students on campus continually enrich their teaching experience.
 
What is it like to live and work on the Fay campus?
Shannon: There is so much talk about how play-based childhood has fallen by the wayside because so much of kids’ time is screened, structured, and scheduled. But with our lifestyle here, we have the exact opposite. Our kids can just hop on their bikes and ride across campus or run over to the playground. On the way home, they might bump into some friends and play an imaginary game in the Sunken Garden, or get invited to toss a lacrosse ball around with some seventh graders. It’s been such a gift for them—and for us.
 
What do you enjoy most about living with the seventh grade boy boarders?
Trey: The seventh grade boys are still so young, and we get to help the kids become the best community members they can be. I like that I get to know them all when they first get here, and then when they move on, I still have that relationship with them. Seventh grade is a lot to manage. They have to manage their school day, sports, family, and roommates. And the kids who were the best at that come back to us in ninth grade as proctors and help guide the next group of seventh graders. It’s a very important job.
 
As teachers, dorm parents, and parents of a Fay grad and two current Fay students, how is your teaching style informed by all the different perspectives that you have on the student experience here?
Trey: You can see the behavioral, cognitive, and emotional stages that the kids go through, and when you see it with your own children and the students you work with, it helps you become a better teacher for that age group.
Shannon: As a school counselor who’s helping students develop the social-emotional skills that they need to be successful community members, it’s helpful to have all the context that I get from doing dorm duty, seeing kids on the quad, sitting with them at dinner, or having students talk to me about their lives and being a part of their lives. I feel really fortunate to have this extra layer of authentic information that some school counselors don’t have.
 
Do you have a favorite Fay tradition?
Shannon: I know I’m biased, because it’s a Mr. Dugger shout-out, but I love the Winter Concert. The music is always beautiful, the community is all there, and then the cookie extravaganza afterwards has such a joyful Sugar Plum Fairy vibe!
Trey: I love the final spring musical performance. On that day, I’m so excited for the community to see the performance and celebrate the kids, and for them to have fun with it. I love it, and the kids love it. My favorite Fay traditions are always performances!
 
Trey, you sing and play percussion, piano, and trombone with several local bands. How does your experience as a performer help you shape the performance skills of the talented musicians you work with at Fay?
Trey: Teaching is what I love to do, but performing inspires my teaching. When I was a kid, it motivated me to see my teachers perform, or when my teachers asked me to perform with them. Students always rise to the challenge of a performance. Usually the last two weeks before a concert, suddenly things start to sound better. Students are anxious, but they’re ready, and all that work they have put in finally comes to fruition. So I love being a performer and showing that to them and having them show that to me. Especially with my older students, I really want them to feel like we’re all musicians and we’re going to prepare for our own parts and take it seriously, and I’m going to treat them like they’re a musical colleague. I perform with them also so they can hear me make mistakes, see me recover, and see how I react to those things. That’s important, because that’s what being a musician is all about.
 
Are there particular Fay traditions and rites of passage that you are excited for your girls to experience?
Shannon: We are so fortunate that there are so many things to do here, whether it’s athletics, music, student council, trying a club, or starting your own. I don’t want to rush our children through Primary and Lower School, but when I think about what I’m looking forward to, it’s all the opportunities that they will have to dive into new interests.
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SOUTHBOROUGH, MA 01772
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