It Started Here

Pomfret wins the first Battle for Route 44.


As the final seconds of the football game ticked down, Pomfret fans let out a collective cheer. The gridiron win sealed the victory of the first Battle for Route 44 — a new rivalry with Millbrook School years in the making.

A few years ago, the former Millbrook Head of School Drew Casertano met Pomfret’s Head of School Tim Richards in Hartford — “the middle” of Route 44 —  to discuss plans for a friendly rivalry between the evenly matched schools. The start of the annual competition was delayed one year (due to Covid) and led to Pomfret setting a high bar.

Mia Fuller ’22 and Linda Done ’23 at the girls varsity volleyball game against Millbrook.

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. The winning design by Nate Finley '24 was worn by Griffins across the Hilltop on game day. Dorms designed spirit banners, which were unveiled during the pep rally and hung in the Dining Hall. Also unveiled at the pep rally were the winner's and consolation plaques. The handcrafted trophies were created by Science Department Chair and Girls JV Volleyball Coach Josh Lake and Science Teacher and Football Coach Brian Geyer in The Foundry, Pomfret's makerspace. Painting and Drawing Teacher JP Jacquet added some flair by painting the prizes. The entire school community gathered on Friday night for a bonfire where sports teams ignited the spirited crowd with their dance numbers.

Griffy pumps up the crowd watching the boys varsity soccer game.

On Saturday, November 13, Pomfret woke up roaring to go. They welcomed the Millbrook Mustangs to the Hilltop and shared a meal in the Dining Hall. Throughout the day, students, faculty, and families lined the sidelines of every field as each team faced off against Millbrook. In the end, Pomfret won the first year of the rivalry — besting Millbrook in seven games to Millbrook’s three and beating their cross country teams at the NEPSTA Divison III Championships.

At the closing ceremony, after accepting the “Better Luck Next Time” consolation plaque, Millbrook's Head of School Jon Downs presented Mr. Richards and Pomfret with The William Peck / Edward Pulling Trophy. He did so wearing a Pomfret sweatshirt and hat, having lost a gentleman's bet with Mr. Richards to wear their opponent's apparel after their loss. It was a bitter pill to swallow as Mr. Downs has wanted to start a rivalry with Pomfret ever since he served as student council president of Millbrook in 1997-1998.

“The weekend went exceptionally well. There was so much school spirit on campus — it made me really proud to be a Griffin. The hard work our athletes put in all season was on display Saturday, allowing us to come away with the win,” exclaimed Student Body Vice President Cate Gallagher ’22. “We're so excited to finally have a rival like many other boarding schools do, and it was so amazing to kick it off this year. I can't wait to see how this tradition will evolve throughout the years and look forward to checking back every fall to see the Griffins take down the Mustangs.”

The crowd cheers on the football team during the Battle for Route 44.


See Photos from the Battle for Route 44 »

Photo credit: Zoe Tahari ’22, Sofia Liu ’24, and Henry Spencer ’24

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