The Battle for Route 44

A new rivalry with Millbrook School is born.

There are some well-known rivalries in the prep school world. Andover vs. Exeter. Deerfield vs. Choate. St. George's vs. Middlesex. Groton vs. St. Mark’s. A few years ago, Head of School Tim Richards met the former Millbrook Head of School Drew Casertano in Hartford — “the middle” of Route 44 —  to discuss plans for a new, friendly rivalry between our two schools. Millbrook is the perfect foil to Pomfret. It’s a school of similar size and stature, guided by a similar set of values, located in a similarly bucolic setting. In fact, Millbrook sits on the same road as us, Route 44, just 110 miles west of here. The start of the annual competition was delayed one year (due to Covid) and led to Pomfret setting a high bar.

The entire school was a part of the preparations for the big day. Mr. Richards held a t-shirt design contest — because all great rivalries deserve t-shirts — and the dorms made spirit banners. Science Department Chair Josh Lake and Science Teacher Brian Geyer handcrafted The William Peck / Edward Pulling Trophy and consolation plaque in The Foundry, Pomfret's makerspace. The School gathered on Friday night for a bonfire where sports teams ignited the spirited crowd with their dance numbers.

On Saturday, November 13, the Mustangs arrived on the Hilltop. Throughout the day, students, faculty, families, and alumni lined the sidelines of every field as each team faced off against Millbrook. If you were able to join us, thank you for cheering the students on and being a part of the Griffin win. We bested the Mustangs in seven games to three and beat their cross country teams at the NEPSTA Divison III Championships.

“I’ve had a front-row seat to three great rivalries: Andover as a student, and Groton and St. George’s as a faculty member. Our friendly competition with Millbrook School is a great new tradition,” said Richards. "We will proudly display The Trophy until we face off against the Mustangs next year and I hope it will stay on the Hilltop year after year." 

Rivalries are fun, but what’s more, they help engender a deep sense of school spirit and community pride. They teach us how to be gracious in victory and sporting in defeat. Perhaps most importantly, they teach us how to cheer like mad for our side without ever feeling the need to boo the other.

See Photos from the Battle for Route 44 »


Photo credit: Zoe Tahari ’22

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