As Mashamoquet Day dawned, the energy of a new school year was in the air. The day began with form bonding activities in the morning, followed by a school-wide field day in the afternoon. Students arrived with the jitters of the first week still clinging to them, the cool, cloudy morning reflecting the unease of fresh beginnings. But as the day unfolded, something shifted — not just in the weather but in the energy that hummed across the Hilltop.

Freshmen exercised their knowledge of their new home in a scavenger hunt that led them across the Hilltop. Sophomores tested their teamwork on Rectory School’s low ropes course while seniors took on “the wall” in the Pomfret Woods. Juniors spent their time exploring Mashamoquet Brook State Park — the namesake of the field day. They developed an appreciation for the park where, for decades, the entire School community spent the day competing in games and events.

By midday, the chilly morning was a distant memory, replaced with sunshine and the warmth of a school coming together. Wearing t-shirts that read "Livin' the Grifflyfe," everyone enjoyed a cookout lunch on The Quad, fueling up for the much-anticipated field day ahead. Led by members of the senior class, the underclassmen divided up into more than two dozen groups and headed onto the athletic fields. Scattered across the western side of the Hilltop were athletic competitions, relays, lawn games, and more. There were the traditional field day events — the three-legged race, egg toss, and sack races — as well as some uniquely Pomfret challenges. These included Baloo and Richards Sketch, which had teams drawing portraits of Head of School Tim Richard, his wife, Anne, and their dog, Baloo, switching artists every thirty seconds. Blanket Name Game required competitors to recall their opponents' names at the drop of a blanket. Golf Cart Push necessitated teamwork to move a golf cart up a hill. No matter the event, the teams were always in for a surprise as they traveled from event to event, and where a member of the senior class explained the rules and guidelines for each competition. 

The culmination of Mashamoquet Day was the tug-of-war competition. The seniors came with a legacy to uphold. They had previously won the event in their freshman and junior years and hoped to add a final tally to their win column. The juniors, who bested the now seniors last year, hoped for a repeat while discussing their strategy in a pre-game huddle. In the first round, the seniors triumphed over the freshmen and faculty. The juniors planned technique of synchronized tugging helped them pull the sophomores across the line. However, when the Class of 2026 faced off against the Class of 2025, their winning strategy was quickly abandoned, and the senior class was victorious once again. 

As the dust settled, it became clear that the day was about more than just wins and losses. The real victory lay in the teamwork, resilience, and school spirit that brought everyone together on the field. By the end of the day, the lingering feeling wasn’t one of exhaustion but of being part of something bigger. 
 

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