“My favorite memory was watching the freshmen overpower the juniors in the tug of war. I was caught off guard and at that moment  it showed me how passionate everybody was about the Winter Carnival” — David Winick ’17

Post holiday break in Wolfeboro, the chilly temperatures outside can bring on a little cabin fever inside but then comes Winter Carnival a few weeks after the students return to campus and teams gear up to compete for the “Headmaster’s Cup.” The name of the winning team is carved onto the Headmaster’s Cup for all to see for years to come. Winter Carnival is a week-long competition among the six academic teams.

This year Winter Carnival was especially memorable because our kickoff events — cake decorating, poster painting, and team area decorating — were followed by the announcement that the entire school would have the opportunity to accompany our prep  basketball team to the TD Garden in Boston to play in a tournament. The campus was abuzz with excitement and chatter.

Monday morning students dressed for the first themed dress up day and at 3 p.m. nearly the entire student body boarded busses for Boston. Students dressed in their best Brewster spirit wear and in dazzling fashion, our Winter Carnival officially began.

Throughout the week we had pie-eating and trivia contests; dodgeball and tug-of war; and several more dress up days. Our final day culminated in the ultimate Winter Carnival event, the lip sync contest. It was a tight race all week as the teams racked up points, but with the lip sync worth the most points, each team was vying for the best performance. Each team’s chosen theme needed to be on full display in their lip sync performance.

Highlights included Mr. Gemmell dancing his best whip and nae nae, acrobatics and backflips on several teams, Neal Woodall’s Ferris Bueller’s impression, Mr. Martin leading the twist, a homage to the Karate Kid, candy throwing, a High School Musical rendition, lightsaber duels, one cameo by a student’s puppy, amazing choreography and some snazzy dance moves by all the teams. It was close competition but for the second year in a row, Team Yau won the Headmaster’s Cup. As Mr. Barnett announced the winner, the seniors rushed the court where Mr. Gemmell was holding the cup. The Winter Carnival ended with excitement, energy, and new memories. The promise of winning the Headmaster’s Cup still clings in the air. There is always next year!

Thank you to the entire Brewster Community who made this year memorable and fun! ~Alicia Childers ’01