2026 NEPSAC Distinguished Service Award: Bob Howe
11/13/2026
Building a lasting legacy as an athletic director for 22 years is an honor Bob Howe wears with tremendous pride and rightfully so.
You have to turn back the calendar more than two decades to fully understand the steady influence Bob left on independent school athletics and physical education across New England during his time at Millbrook School, Loomis Chaffee School, and Deerfield Academy. For the same kid who spent the first 19 years of his life living on the campus of Loomis Chaffee, first as a faculty child and later as a student-athlete, it’s only fitting that Bob received the NEPSAC’s 2026 Distinguished Service Award thanks to his significant contributions to preparatory schools in New York, Connecticut, and Massachusetts.
“I have always felt that athletics, or any form of extra-curricular involvement, is so important to anyone’s high school experience and personal development,” said Bob Howe, who retired from Deerfield Academy at the end of the 2025-2026 academic school year.
“Receiving the Distinguished Service Award from NEPSAC means a great deal to me. Having the opportunity to help maintain, redefine, and safeguard this idea within such an elite group of schools has been incredibly rewarding for me. This experience has also connected me with talented and dedicated Athletic Directors from other schools, many of whom have become life-long friends. For this too, I feel very fortunate.”
With past recipients recognized for their enthusiasm, dedication, leadership, and vision in shaping athletic and physical education programs, Bob joins an esteemed group of award winners who designed their own blueprint on how to construct a better overall NEPSAC experience for students, coaches, and the school community. After graduating from Loomis Chaffee (1976-1980) and Hamilton College (1980-1984), Bob went to work for a custom home builder in southern Vermont before starting his own building business, Howe Builders. A new opportunity and career led Bob and his wife, Amanda, to make the move to Millbrook in 1992, where Bob wore many hats as the Director of Physical Plant and Head Hockey Coach.
In 2004, Bob took a leap of faith by returning to his alma mater as the Athletic Director at Loomis Chaffee.
“I was taking a chance for sure. I suppose it came as a bit of a surprise to many that I was hired as I had no previous experience as an athletic administrator,” Bob recalled about those early days at Loomis.
“I loved athletics. I played three sports in college for all four years – soccer, hockey and lacrosse – and I captained all three teams in both my Junior and Senior years. I had also recently built a successful hockey program at Millbrook, so Loomis gave me that opportunity to bring my love for athletics and my experience as a manager to their campus for twelve years.”
The next decade as Athletic Director at Deerfield Academy, however, almost didn’t happen.
“In 2016 Deerfield Academy called me asking if I knew anyone who might be interested in becoming their next A.D. I gave them several names of good candidates I knew. After reading more carefully about the Deerfield job offer I decided to apply myself. Again, I got lucky and got to spend the last 10 years of my school career at Deerfield. I’ve always felt that having worked at three different schools gave me the opportunity to develop a broader understanding of schools’ needs and a better understanding of what the issues were at more levels of school size.”
To this day, Bob credits both longtime Athletic Director, Mark Conroy (a Distinguished Service Award winner himself in 2024), and former Millbrook Head of School and his former teacher and coach at Loomis Chaffee, Drew Casertano, for being mentors, motivators, and positive influences on shaping his career.
“Working under Drew, his vision and the way he approached school-life was very transformative for me and my family. He made me want to be a person who worked in school athletics.”
The admiration is clearly mutual.
“In his years at Millbrook, Bob created a sense of team in his department and throughout the school, and he enhanced a campus that sorely needed his exceptional commitment and attention to detail. He built a competitive hockey team the right way and, to this day, his players love him,” admitted Drew Casertano, who recalled meeting Bob as a Junior during Drew’s first year teaching at Loomis.
“This was one of the best decisions I made in my 31 years at Millbrook. Bob is the very best boarding school person, and for those of us who have lived life among the adolescents, there is no higher praise.”
In addition to his duties as Athletic Director, Bob also served as NEPSAC President (2017-2019) and was an active Board member until his retirement in 2026. It was in those leadership roles and meetings that Bob learned, grew, and intently kept a focus on the greater good of NEPSAC.
“The athletic landscape has changed so much during the time I’ve been involved,” Bob said when pondering his vast accomplishments.
“I’d have to say my proudest moments came when we’d have robust discussions involving policy change or looking to do something better to help serve our association better. In NEPSAC there are over 180 member schools with a broad range of size, geography, gender composition, and facility. One area of growth I’m particularly proud of is the expansion of the number of female representation on the NEPSAC Board. When I arrived as a young Board member back in 2006 the composition of the Board looked very different than it does today. I’m also very proud of the fact that as a Board we always looked for solutions that did ‘the greatest amount of good for the greatest amount of schools’, to borrow a Mark Conroy quote frequently discussed at meetings. I enjoyed working closely with Mark and following him with the District IV leadership and consequently onto the Board. He was the person who got me invested in leadership outside of my school.”
Pausing for a moment, the 2026 Distinguished Service Award winner and former Athletic Director of 22 years quietly considered how his time working within independent school athletics and physical education made him a better person after all those years removed from being an in-experienced first-year AD at Loomis.
“I think I have become a better listener. I became a problem solver and also a stronger community member. When you work with colleagues who are neighbors and you have shared school and athletic activities together, the reward is you get to work with very talented people.”
If you are looking for Bob Howe these days, he won’t be hard to find with retirement in full swing.
Just stop by the Rochester Ice Center in Fairport, New York and ask for the man fondly called “uncle Bob” among his dedicated co-workers. He’ll be on a Zamboni resurfacing the ice for upcoming skating and ice hockey play at the rink. It’s where his heart belongs. In between projects at home, scenic bike rides with his wife Amanda, gym workouts, and a long list of hobbies that await, this is Bob’s new normal.
“It has helped center me. It has been an adjustment having lived on campuses and followed a predictable schedule for many years. I find having all the time in the world can be both exhilarating and overwhelming at times,” said Bob when asked about trading the ups and downs of a full athletic season in the NEPSAC for his part-time Zamboni driving duties.
“This is the first job I’ve had where I clock in and clock out with each shift. I’m happy where I am right now.”
ADDITIONAL LINKS:
Please view the photo gallery here.
Please view the 2026 program here.
Please view the 2026 NEPSAC Annual Meeting website here.