Maren Kelsey Awarded Pennypacker Prize

The Pennypacker Prize is a special way for us to recognize a Winsor teacher of great promise. Created in 2002, the award is “given annually in the name of Henriette Pennypacker Binswanger ’52, with respect and admiration for the educational excellence of the Winsor School and the memory of an extraordinary experience.” Henriette attended Wheelock College after graduating from Winsor and went on to earn her MEd. from Harvard. A fervent advocate for women’s rights and environmental preservation, she loved classical music, dragonflies, mid-coast Maine, and was described as having a “sense of absurd humor.”

The Pennypacker Prize is awarded each year to a teacher who is in at least their third year of full-time teaching at Winsor. It’s intended to encourage the recipient’s continuing educational growth and development. This year’s winner joins impressive company. Our list of past recipients includes Erin Calamari, Josh Constant, Julia Harrison, Jeremy Johnson, Denise Labieniec, Dana Martin, Kim Ramos, Ken Schopf, and Lisa Stringfellow, to name a few.

The following award presentation - which remains a surprise until awarded! - was given by Head of School Sarah Pelmas during the faculty and staff appreciation dinner on Thursday, November 19, 2020.

This year’s winner distinguished themselves by making me wait. When they interviewed here, and when all the reference checks were completed, I sent an email asking whether we could talk that evening or the next day. During our conversation, in which I offered them the position, this teacher asked me to send the daily schedule, and asked a few additional questions. All perfectly reasonable. I sent everything that was requested. And then I waited. 5 days.

Well, obviously it worked out, and obviously it was worth the wait. But my point here is: this person doesn’t do anything hastily or without serious thought. This is a considerate, considered person, someone who speaks with care, who prepares meticulously, and who listens deeply and with their whole heart.

Almost from the first month this teacher started at Winsor, a little over two years ago, students and colleagues alike have been full of praise. In fact, when I reached out to students to ask them to write me a little something about their teacher, I asked 15 students thinking I might get 5 timely responses back. But no, not this time: every single one of them responded--and some almost immediately.

Why such enthusiastic and heartfelt respect and admiration for this person? Well, some of the words used are: welcoming, open, always learning, fun, at ease, trusted, respectful, joyful, encouraging.

When I reached out to colleagues to get a fuller picture, Alice Stern, director of the Virginia Wing Library, said, “In my 20+ years at Winsor I have seen many wonderful colleagues come and go but [this teacher] is truly one of the most amazing. Their respect for their students is palpable, and they have in their short time at Winsor become a ‘trusted adult’ for so many of them. I’ve had the pleasure of working with [this teacher] on a few initiatives and I am astounded at how they can put into words a thought that I have barely formed. And they do this with such humility! We are so lucky to have [this teacher] at Winsor.”

It’s easy to agree with Alice on this one. Our recipient has quickly become someone we all feel we have known for some time, someone who has jumped into the curriculum, the clubs, the professional development, and the overall life of the school with such commitment and good humor that it seems we have been working together for years.

More specifically, this teacher came to us having worked with 3-6 years olds in a preschool and a headstart program, then moving on to work with middle and upper schoolers at summer camps and after-school programs, and finally landing as an English teacher at the Park School. For their two years at Park, this teacher did everything from teaching Health classes, to developing after school activities, to leading the GSA club, to playing in the band for the musical--and also teaching both 7th and 8th grade English. Lucky for us, Park was phasing out its 9th grade program and this teacher came to us. And, as I said, not without thinking it through carefully! And I haven’t yet mentioned that this teacher also likely has a career as a novelist ahead of them, having won their college’s prestigious undergraduate fiction prize.

Here at Winsor, in the classroom, our award winner has a huge toolkit, and does everything from “grammar speed dating” to deft management of complex discussions around identity. They consistently turn the discussion over to the students, but in a practiced way that involves all students and pushes the class to think in more complex ways about apparently simple moments in novels or poems. Colleagues are quick to point out this teacher’s tremendous instincts and generosity with time and brainstorming. Laura Beebe, English faculty, says they are “deeply thoughtful about pedagogy” and “uber organized.” English Department Head Courtney Jackson cites their “warmth, voice, and expertise,” and particularly praises the way this teacher connects with students in the classroom.

We have already benefited from this teacher’s work with Spectrum and WCCR, their fabulous professional day panel on the multiple ways that gender and sexual identities and expressions work, and even their star turn on guitar with Carey McKinley for Mary DePalma's sign language song “Swimming to the Other Side” performed at last year’s Faculty/Staff Variety show!

Universally, colleagues point to this teacher’s winning combination of flexibility and creativity in curriculum design, DEI expertise, clear commitment to knowing the whole student, and great sense of humor. Arriving early in the morning and staying late into the evening (pre-pandemic) to watch games or theater productions, this teacher does indeed know the whole student and celebrates them.

As Katina Handrinos ’25 puts it: “[This teacher] is a person of substance and spirit and has created an atmosphere unlike any other inside of our classroom. As a part of one of their Class IV English classrooms, I always feel relaxed and at home… [They] reassure us and never stop cheering us on throughout any assignment. No matter whether the lesson is about long descriptive poems, grammar, or Shakespeare, [they] somehow always makes us laugh, discuss, and learn from any of these topics. [And this teacher] even takes our lives outside of school into consideration when giving us assignments and nurtures open and honest conversations…. I feel incredibly lucky to be in their class, and I feel as though I have already learned so much from them, even only 3 months into the class. I’m so excited that they are receiving this award, because they truly deserve it, and I know that if you talk to any one of their students, everyone would agree.”

I’d hate to say that this teacher has already peaked, at such a young age, but there may be no better moment than the recent debate about whether a hot dog is a sandwich. If you were there, you know that a hot dog, according to this teacher, is definitely a sandwich! Bread and meat, eaten with the hands, why make arbitrary boundaries where none are needed? Why quibble about whether a hot dog bun is one piece of bread or two? Why limit ourselves to narrow definitions?

I can’t end without giving you a sense of the range of student praise I’ve received.

Casey Carlisle ’25: “They create a class environment that makes room for every voice to share. When I ask questions, they always respond with a caring and thoughtful response.”

Liana Min ’26: “I can truly say that [this teacher] is one of the most extraordinary teachers that I've ever had the privilege of learning from.”

Ali Pynchon ’26: “[This teacher] has given me a new excitement for English class that I didn’t think I could ever have. They have made English a fun and energetic place and I am excited for the classes to come.”

Sophie Fleishman ’25 and Nell Sparks ’25: “They...do a really good job of having a great balance between fun and work, so classes are enjoyable but we still get things done.”

Theo Zarrow ’26: “[They] bring out the best writer and thinker in all of us and that is why there is no other person better to receive this award.”

Amelia Kwak ’25: “They have consistently shown that they care deeply about every single one of their students, both as learners and as humans. They teach us respect and kindness, and they unquestionably lead by example.”

I can think of no higher praise than what our students have to say. So I ask you to join me in congratulating and celebrating this year’s Pennypacker Prize winner, Maren Kelsey!

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