Mr. Tom Herold, instructor of English, has taught for over forty years. After graduating from Dartmouth College in 1983, he began his career at Rectory School in Pomfret, CT, where he taught English and Social Studies and coached soccer and lacrosse. Mr. Herold then taught at Hill School in Pottstown, PA for 10 years and Culver Academies in Culver, IN for three before coming to Hotchkiss in 1999. This year marks his 27th at Hotchkiss.
In addition to teaching across the entire curriculum in the English department, he has coached Varsity and JV Boys and Girls Soccer, and JV and Varsity Boys Lacrosse.
During his career, Mr. Herold earned two advanced degrees through summer study: a M.A. in English in 1993 from Middlebury Bread Loaf School of English and a Master of Education concentrating in educational leadership from Teachers College, Columbia University in 2005.
Mr. Herold was also a Hotchkiss parent for eleven consecutive years, from 2013 to 2024. All three of his children were alums: George Herold ’17, Leslie Herold ’20, and Jack Herold ’24.
What led you to teach at the school?
Mrs. Herold and I were interested in moving back to the Northeast. At that point, when I started looking for a job in 1999, we were happily employed at Culver.
Both Mrs. Herold and I knew boarding schools very well: Mrs. Herold through her experience as a former student at St. Mark’s and mine as a teacher. So, prior to coming to Hotchkiss, I had many connections from working at other schools.
There are two people especially that I would like to mention: John and Christy Cooper. Mr. Cooper used to teach math at Hotchkiss and his wife, Christy Cooper, taught in our English department for many years and was a school administrator. They clued me into the fact that there was an opening and it was a good time to apply.
When we came to Hotchkiss, Mrs. Herold and I were brand new parents. We had an eight- month-old baby boy and it was a really wonderful time in our lives together as a couple. We knew that we wanted to be apart of a boarding school community.
When we moved to Hotchkiss, we moved into Coy Dormitory. Mr. Chris Oostenink and Ms. Carita Gardiner, who were also in Coy back then, were very welcoming and fun to work with.
The boys that lived in Coy were just great—not just the 9th and 10th grade boys who were living in the dorm, but the proctors as well.
We fell in love with the school that way, through our experience as residential faculty.
What have been some of your favorite classes to teach?
I’ve enjoyed all the courses that I’ve gotten to teach and all the students of different ages.
With ninth graders, it’s a very exciting time getting to know your new school and thinking about the path of your high school career. And so being someone who can help those students learn about the possibilities here and learn more about themselves and what it is they might accomplish is certainly really fun.
What parts of your experience here have been the most meaningful?
Watching our children go through Hotchkiss and gain from their experience and struggle at times, too. I’m very proud of the fact that Mrs. Herold and I were able to give that opportunity to our children by working here.
What do you think the school stands for?
I think it stands for the pursuit of excellence and also finding personal fulfillment by taking on new challenges and learning more about yourself. I see that over and over—it’s a consistent theme. Kids come to Hotchkiss, and they grow and find out a lot about what they like and maybe what they don’t like so much.
What will you miss most about the school when you retire?
I will miss the companionship of my fellow teachers in the English department—going through the work that we do together and being there to support each other and learn from each other. I’ll still have those relationships and friendships.
Mrs. Herold is going to continue to work here, so I’m not moving away. I’ll still be able to see those folks and interact with them, but it’ll probably be a lot different.
What advice would you offer to students?
Don’t forget to have fun. Your high school years will go by quickly, and you don’t want to spend the whole time in a classroom in the English wing grinding away.
