Head’s Holiday, an Annual Tradition

Head’s Holiday, an Annual Tradition

Elaine Loft, Staff Writer

Each year since 1967, Derryfield students have been treated to Head’s Holiday–a surprise day of fun and community spirit. The Head of School secretly chooses the date, and the announcement is made first thing in the morning, usually during an (otherwise) run-of-the-mill school assembly. 

Following the annual, and exuberant Halloween activities of October 31, the Community Meeting on Monday, November 4, seemed to be following a familiar agenda. Head of School Andy Chappell congratulated the Middle School field hockey team, who had won the Tri-County Championship over the weekend. Next he talked about how the Isakovich-Critz Family had established a Fund for Community Enrichment, reminding the audience that the fund had supported the visit of author Joshua Davis. Chappell then shifted gears, and announced that the program that morning would be “quite different from what we have experienced so far this year…” He didn’t get to complete his cliffhanger—as he was interrupted by Derryfield mascot Moose the Cougar, who bounced down the auditorium steps, then got down on one knee to proffer an envelope bearing a special message. Chappell kindly spoke on behalf of Moose (a mammal of few words).

“We’ve had a busy and productive fall; from the first day of school until now we have come together as a community to support one another and to bring tremendous energy to our classes, athletic contests, Spirit Week, Day of Giving, Day of Service, Halloween and so much more. We have a tremendous amount to be proud of, and so I, Moose the Cougar, along with Mr. Chappell officially proclaim that today, Monday, November 4, 2024, is Head’s Holiday.”

The student body, faculty, and staff erupted in cheers! The special program was led by Gerard Senehi, who is known as The Experimentalist. Chappell informed the audience, “Mr. Senehi is known to open the door to the vastness of what we don’t know…to inspire the audience to suspend limits of how we think… to evoke a sense of wonder and imagination…to see beyond our differences as human beings and to consider new ideas and new solutions.” Indeed, Senehi’s act kept the audience guessing for a full hour.

After the conclusion of the mind-bending program, Greg Lange, Events and Engagement Manager outlined the schedule of activities, including human bowling, black light games, a petting zoo, and Family Feud. Favorite fall foods of pumpkin whoopie pies and apple cider were on offer for the afternoon snack.

When asked about his favorite activity, Milan Bartoli ‘29 offered, “I liked that we got to go out on the turf, and play with our friends.” Margo Blake ‘31 enthused, “The bounce house was so cool, ‘cause we got to race one another.” Students sitting on the ground, petting docile bunnies and tolerant chickens observed, “This is like meditation–I feel so calm.”

Head of School, Andy Chappell, concluded,

“Yesterday was a joyous day filled with laughter and boundless energy as students and faculty gathered to play and share in the simple happiness of being together. I loved seeing everyone having fun, spending time with friends and enjoying my holiday; Head’s Holiday.”

The spontaneous day of fun and games is more than a cherished tradition, it is also a Derryfield “rally point,” offering both a release of energy and a celebration of community.

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