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A woman in snow with pink earmuffs smiles and has open arms over an announcement for no school.

Among the many anticipated traditions at Emma Willard School is Principal’s Play Day: a surprise holiday started in 1955 announced by the Head of School and kept secret until the day before. While students enjoy the unexpected day without classes, the day includes a series of surprise activities open to the school community.

For several years the holiday has been announced in the spring: leading current students’ suspicions to largely be dormant until the weather on Mount Ida turns warm, and mostly to think it will happen on a Friday. This year, the Student Life Department and Jenny Rao conspired to set the holiday in the doldrums of winter. 

Winter sports enthusiasts Megan Labbate and Mary Hunter (of the Science and English Departments) set up the announcement with competition: which faculty member is better at winter athletic activities? They answered the question with a video that hit mailboxes at 3:30 p.m. on Monday, January 29, featuring a special announcement at the end from Ms. Rao: Principal’s Play Day!

The next day, amid coordinating transportation, finding equipment, and sorting piles of winter gear, students, faculty, and staff had the chance to hit the slopes together: 

A woman taking a selfie with teenagers, wearing winter clothing and on a mountain.

Head of School Jenny Rao and Dean of Students Shelley Maher with several seniors during PPD.


A woman taking a selfie in a snowy setting with students.

Jenny Rao with students at the winter activities for PPD!


A woman poses for a selfie with a group of students in winter gear.

Jenny Rao poses for a selfie with students on PPD!


A group of people in snowy woods posing for a photo in snowshoes.

Snowshoeing was among the activities for the day!


Though this year’s winter fun was a departure from recent excursions, the spirit of community, fun, and an opportunity to get off campus and do something new remains the same. Principal’s Play Day 2020 featured a plethora of physical activities from rock climbing and axe throwing, to aerial yoga and classes at Orange Theory


A selfie of several people skiing and smiling.

Faculty and staff enjoying the slopes on PPD!


Last year’s festivities included a day at the world’s largest indoor roller rink, Guptill’s Arena, and live music festival-style came to campus in 2021. Many still talk about the PPD on campus that included a dunk tank, and legendary is the ‘Headmaster’s Holiday’ in 1969 when Bill Dietel landed on the senior triangle in a helicopter, arms laden with daffodils for each student. 

The roots of Principal’s Play Day are in ‘Headmistress’s Holiday,” a tradition started in 1955 by Headmistress Ann Wellington on her birthday, and repeated annually on a different, surprise, day marked by “a complete absence of regulation and routine.”

A passage in Trudy Hanmer’s Wrought with Steadfast Will: A History of Emma Willard School details Ms. Wellington’s explanation of the day:

She explained to the board that “food was available for protracted hours in the morning, and a variety of recreations planned for the entire day.” The results for the students, she concluded, were “slight fatigue, maximum happiness, a tremendous boost for general school morale,” and perhaps most satisfying to her, “the verified suspicion that the headmistresses and teachers were, after all, human.”  (425)

It might not have been entirely a day of rest, but the jolt of energy a surprise holiday brings allows students and faculty to leave the classroom for fun, recreation, and connection! 


Find more interesting stories about Emma Willard School on our Newsroom page.