Wakefield Thought Leaders

Curiosity, Meaning, and Service: Rachel Squire Munson ’06 Addresses the Class of 2026

Tue, 23 Jun 2026 04:00:00 +0000

Curiosity, Meaning, and Service

Rachel Squire Munson ’06 Addresses the Class of 2026

Each year, Wakefield welcomes a distinguished alumna or alumnus back to campus to address the graduating class at Commencement.

On Saturday, May 23, 2026, Rachel Squire Munson ’06 returned to the Hill to share her journey with the Class of 2026. Drawing on experiences in public service, consulting, and higher education leadership, Rachel reflected on the values she first developed at Wakefield and encouraged graduates to embrace curiosity, seek meaningful work, and serve their communities.

Read her full Commencement address below.

^{The following remarks were delivered by Rachel Squire Munson ’06 at Wakefield's Commencement ceremony on Saturday, May 23, 2026.}

Good morning!

Thank you to Ms. Harper, the Wakefield faculty and administration, the Board of Trustees, and the Class of 2026 and your families for having me here today.

I know it’s a bit of a cliché, but it doesn’t feel like so long ago that I was on a stage like this one at my OWN graduation, delivering a co-valedictory speech to the 16 other Wakefield students in my graduating class.

I always thought alumni commencement speeches were reserved for...old people. 20-plus years out of school, mid-career, house, spouse, a couple of kids, and a bedtime of 9:30. Then I realized... that’s me. Right down to the bedtime.

It was a genuine surprise and a true honor to be asked to speak today, and graduates, I promise I’ll try my best to impart some of the insights I’ve gained since my own time at Wakefield. It may surprise some of you to learn that the first 4 of my 14 years as a Wakefield student were actually spent in... a nursing home. That’s right, before there was this beautiful campus with sparkling new facilities for the arts and athletics, our day was spent down at Marshall Manor.

I know some things have changed since then — larger enrollment, more robust curriculum, and maybe even more relaxed uniforms (I heard about the seniors wearing solid polo shirts – nice work). But it’s clear that some of the traditions and elements I remember most — the parts that make Wakefield unique — have stuck around.

20 years ago, the last time I was up here, I poked a little fun at the special things about Wakefield — what I called the “exasperating quirks.” All school assembly. Senior lounge. Talisman. An entire class period on grammar. Great 100’s. Those are happy memories. Wakefield was — Wakefield is — an incredible place to grow up. And I’m actually so happy to know that some of those things are all still major parts of the Wakefield experience. But I think the small, tight-knit community, along with what you all call the Wakefield Way — what we used to call the courtesies — are the real things that make this place so special.

Whether you know it or not, all of you graduates have internalized a set of guiding principles and a sense of communal responsibility that you’ll take with you wherever you go. That’s something to be immensely proud of.

And it’s not just the graduates who should be proud, I should add. If you’re a parent, you can be proud knowing that the sacrifice and hard work it took to get your kids here and to keep them here was worth it. If you’re part of the school’s faculty and administration, you have nurtured and cultivated another set of curious, respectful, and service-driven leaders — graduates with virtue and wisdom.

Two of those dedicated teachers who shaped me are even in this room today! Mr. Genther has been teaching art at Wakefield since I was little, and somehow, he is still here, still everyone’s favorite, still doing it. In his class, we got to play CDs (what you guys now call Spotify), and we got to choose the albums. That sounds like a small thing, but for a middle schooler who was not the most confident picking up a paintbrush, it made the room a lot easier to be in. He always gave you just enough room to stretch into something uncomfortable, but he never made you feel like you were failing at it. And I am sure that his art room is now one of your favorite places to be on campus, too.

And Mr. Zontine, my senior English teacher, used to quiz us... on rock and roll trivia. As far as I could tell, this had nothing to do with the syllabus – and I think that was kind of the point. He would push our answers as we discussed the great canons, and make us defend what we thought. He taught us some of the zaniest Words of the Day (WODs). One day, he asked us to write down, anonymously, what we thought God was and looked like. There was no right answer – but he just wanted us to have one. In a very “senior English teacher” sort of way, he made us start thinking about who we would want to be in this world.

But back to the graduates in the front row. I was asked to share some advice with you all today — and so I have two of my own WODs for the Class of 2026. One of those words is already core to the Wakefield Way: Curiosity.

You all are entering college next year – congratulations! You wrote two English thesis papers, you took your APs and DEs, and all of that hard work has paid off. But underneath the grades on your transcript, behind the SAT scores, and putting aside the “outcomes” that sometimes seem most important, Wakefield has taught you to listen and to learn. And next comes the fun part.

You will soon discover the pages and pages of classes to choose from in your college course catalog. It’s overwhelming. Classes across agriculture and architecture, marketing and management, sociology and statistics, and Spanish – you get the picture. The opportunities for curiosity are endless.

Here’s one piece of concrete advice for you: take some academic chances. Spend some time scrolling through the catalog. Something catch your eye? Pause for a second – be curious. A professor mentions something in a lecture that doesn’t match what you thought you knew? Go find them after class – be curious. That instinct, that small moment of wait, really? That's the thing Wakefield has been building in you.

I'll tell you what happened when I followed that curiosity. I went to college in Philadelphia, and in my second year I signed up for a class that caught MY eye about architecture and the city in the 20th century. It was taught in a department I had never heard of called Urban Studies. I was curious, so I signed up. I wanted to understand this city I'd landed in a little better. I ended up majoring in it.

Before I knew it, I was interning in the New York City Mayor’s Office. After I graduated, I went back to City Hall as a full-time employee, working my way up the ranks. When Superstorm Sandy struck the City in 2012, I was entrusted to lead a program that helped thousands of homeowners use public funds to rebuild and stay in their homes. My life’s work had become learning more about my city and how to make it a better place — all due to that spark of curiosity.

And that brings me to my second WOD for the Class of 2026: meaning.

As you open those doors, try new clubs and classes, explore majors and minors, and ultimately look for that first job or two after college, I hope that you find work that truly calls to you — a mission that you believe makes our world, or your city, or your community, a better place. This could look different for each one of you – going to nursing or medical school to help people at their moments of greatest need; Training as a social worker and protecting the rights of the vulnerable; Becoming a teacher and setting a child on a life trajectory they wouldn’t have thought possible. When you find work with meaning, you see the impact of your work right in front of you — in the faces of the people you help, in your community.

I’m a parent of two daughters now—one is sitting right there (Hi, Dori!), and I feel grateful knowing that my small contributions will outlast me. They will make not only my city, but also her city, better, too. To me, that is what meaning feels like. And public service is the clearest path to meaning that I know.

So that's what I've got. Curiosity, meaning, and public service. From someone who went to elementary school in a nursing home. And somehow ended up here. The residents of Marshall Manor would have loved you all, by the way. And I think that maybe those nursing home residents, with the wisdom of their years, would have told you the same thing I’m telling you now: Be curious, search for work that has meaning, and find a way to be of service to your community.

Go forth, Class of 2026. You're ready. And when you get to college, call your parents. Trust me, they’ve earned it!

Congratulations!

About the Speaker

Rachel Squire Munson ’06 graduated from Wakefield in 2006 and earned a B.A. in Urban Studies from the University of Pennsylvania and an M.B.A. from the Wharton School.

She began her career as an Urban Fellow in the New York City Mayor’s Office and later helped lead post-Hurricane Sandy housing recovery efforts and initiatives to improve services for millions of New Yorkers. She subsequently spent six years at Boston Consulting Group, rising to Principal and advising public- and private-sector leaders on organizational transformation, strategic planning, and COVID-19 recovery.

Rachel currently serves as Vice President for Strategy and Operations at New York Law School. She lives in Brooklyn with her husband and their two daughters, Dori and Poppy.

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Scenes from School: "Words and Ideas Can Change the World"

Mon, 06 Apr 2026 04:00:00 +0000

Scenes from School:
"Words and Ideas Can Change the World"

~ John Keating from Dead Poets Society

At the Junior Thesis Forum, students engage deeply with literature—crafting arguments, defending ideas, and discovering the power of their own voice.

By Matt Zontine, Academic Dean & English Department Chair

About This Series: Each month, Wakefield’s Upper School Academic Dean and Middle School Advisory Dean share reflections on the life of the school — moments of discovery, collaboration, and joy that unfold beyond the traditional classroom. We’re pleased to share some of these stories here, offering a glimpse into the spirit of learning that defines Wakefield.

On an evening in early March, the 11th-grade class experienced one of many rites of passage that Wakefield students encounter: the Junior Thesis Forum. Having written a twelve to fifteen-page research paper on a novel or play of their choosing, the forum is the culmination of all the work students have completed in their Composition course this year.

As Mrs. Keturah Maraska explained in her opening remarks, “In developing their thesis statements, these students took the opportunity to think for themselves and trust their own interpretations of the work. But the path to this evening was not always a straight line. The process has been both exciting and difficult. There were times when this night felt out of reach. These students had to restart, revise, and edit their work again and again. They learned that finding your own voice takes a lot of persistence and hard work.”

The forum took place at two locations, with each hosting two sessions. In the library, Mrs. Maraska moderated the sessions on “Gender Expectations and Defying Domesticity” and “History and The Power of the Emblem.” In the lecture hall, Mr. Zontine moderated sessions on “Dystopia and the Architecture of Control” and “Guilt, Regret, and the Fractured Hero.”

The forum consisted of two parts: the presentation and the Q&A segment. Each student read a two to three-minute speech in front of classmates and family guests that encapsulated the focus of their paper, and then they were given two questions to answer regarding their work.

Below is a sample of questions that students were asked.

In Jane Austen’s Pride and Prejudice, the author seems to reward Elizabeth with love and wealth for staying true to her virtues. Is Elizabeth’s happy ending a form of wish-fulfillment for Austen, or is it a rhetorical tool used to convince her readers that a woman's integrity eventually pays off?
The fence in August Wilson’s Fences serves as both a barrier and a prison that Troy creates to protect his family. Rose wants the fence to keep her loved ones in, while Troy uses it to keep death and phoniness out. At the end of the play, did the fence protect the family from the world, or did it just isolate Troy from the people who loved him?

Although the evening is not without its stress for the junior class, the experience underscores the magnitude of the students’ impressive accomplishments. Jacob N., who recited his speech from memory, prepared for the evening by “reading his script over and over again. I felt more comfortable [memorizing the speech], not worrying about looking up and down.”

When asked to explain her approach, Annabelle P. took a fatalistic perspective, quipping, “I had no choice. I just practiced as much as I could, and if I messed up, I knew to keep pushing forward.” She continued that “as much as it tortured” her, she feels that the Junior Thesis forum has “value.” For next year’s junior class, she offers the following advice: “Having confidence in yourself comes from knowing what you are doing.” Thus, practice, practice, practice.

Click on the link to see the titles for all of the Junior Thesis papers.

In the Spotlight: Wakefield’s The Play That Goes Wrong Featured in Middleburg Life

Wed, 01 Apr 2026 04:00:00 +0000

In the Spotlight: Wakefield's The Play That Goes Wrong Featured in Middleburg Life

This piece highlights the article published in Middleburg Life & Hunt Country (April 2026):
“The Play That Goes Wrong”: Dr. Toby Brings the West End Hit to Wakefield
By Diane Helentjaris

Published in: Middleburg Life & Hunt Country - April 2026

Wakefield’s upcoming Upper School production of The Play That Goes Wrong is getting attention beyond campus—recently featured in Middleburg Life.

“The Play That Goes Wrong”: Dr. Toby Brings the West End Hit to Wakefield spotlights Wakefield’s upcoming Upper School production of The Play That Goes Wrong and the creative leadership behind it.

Directed by Dr. Toby Chieffo-Reidway, the production brings one of the most celebrated modern farces to the GLO Theater—a high-energy comedy known for its perfectly timed chaos, collapsing sets, and laugh-out-loud mishaps. But beyond the humor, the story highlights Dr. Toby’s deep commitment to theater education and the transformative role the arts play in students’ lives.

With a large student cast and crew bringing this ambitious production to life in the GLO Theater, it’s shaping up to be one of the biggest—and most entertaining—performances of the year.

Read the full feature in Middleburg Life, then grab your tickets—you won’t want to miss this one.

From the Owl's Nest: Familiar Faces Worth Celebrating (Spring 2026)

Wed, 01 Apr 2026 04:00:00 +0000

From the Owl's Nest: Familiar Faces Worth Celebrating

Wakefield School Alumni Newsletter – Spring 2026

This newsletter is designed to reconnect our Alumni with Wakefield through stories, updates, and opportunities to engage—with fresh energy behind the work and big celebrations on the horizon.

Spring at Wakefield always brings a certain kind of energy—students deep in their work, the campus coming alive again, and familiar faces finding their way back.

Juniors have just presented their theses, seniors are putting the finishing touches on their Capstones, and Upper School students have set off on this year’s spring break trip through Australia and New Zealand. In the Lower and Middle Schools, classrooms are buzzing with projects, performances, and the rhythm of the season as Field Day approaches.

This season, we’re thinking especially about the people who shape Wakefield—past and present—and the connections that continue long after leaving.

Here’s what’s been happening—and how you can be part of it.

A (Very Quiet) Surprise for Mr. Genther

Help Us Celebrate His 40th Year at Wakefield

If you had Gary, you probably remember two things:
He'll duck and cover whenever the camera is pointed at him, and he doesn't love attention.

So naturally, we’re trying to do something for him anyway.

This year marks his 40th year at Wakefield, an extraordinary milestone for a teacher who has shaped generations of students not just during their time here, but long after. For many alumni, he’s the one you remember first and the one you come back to see.

We’re gathering notes, memories, and photos from alumni to share with him at the end of the year—a collection of stories from the students he’s taught over the years.

No big spotlight. No speeches. Just something meaningful, and very him.

If you have a memory, a photo, or something you’d want him to read—we’d love to include it.

Share a Note for Mr. Genther

From the Class of ’06: A Voice for Commencement

Rachel (Squire) Munson ’06 will deliver this year’s Commencement address, returning to campus in a meaningful full-circle moment as the Class of ’06 celebrates its 20th.

Rachel currently serves as Vice President for Strategy and Operations at New York Law School, where she works on big-picture strategy and day-to-day problem solving to help the school thrive.

Before joining NYLS, she spent six years at Boston Consulting Group, advancing to the role of Principal and advising public- and private-sector leaders on organizational transformation, strategic planning, and COVID-19 recovery. Rachel began her career as an Urban Fellow in the NYC Mayor's Office and went on to spend several years in City government, helping lead post-Hurricane Sandy housing recovery programs and working in the Mayor’s Office of Operations to improve services for millions of New Yorkers.

She earned her MBA from the Wharton School of the University of Pennsylvania and her BA in Urban Studies, also from Penn. Rachel lives in Brooklyn, NY, with her husband and two children, Dori (4) and Poppy (1).

We’re honored to welcome her back to Wakefield to share her perspective with the Class of 2026, sitting where she once sat 20 years ago.

Wakefield's 30th Anniversary Gala Auction Goes Online—Join From Anywhere

Bidding opens April 6 and closes April 11 at 7:30 PM

Wakefield’s Sparkling Speakeasy 30th Anniversary Gala Auction is going fully online for the first time—so no matter where you are, you can be part of it.

Starting Monday, April 6, 40+ items will be available to browse and bid on, including unique experiences, family adventures, and Wakefield favorites.

One item we’re especially excited to share with alumni:

2027 Alumni Weekend VIP Experience: Gold Cup + Private Reunion Party
Gather your classmates and return to campus for Wakefield’s first annual Alumni Weekend (April 30–May 1, 2027), then celebrate in style on Saturday at the Virginia Gold Cup with your own rail-side tailgate next to the Wakefield tent and a private reunion cocktail party back on campus for your group.

This is the perfect package for those classes celebrating the big milestone reunions—40th, 30th, 20th (Classes of ’87, ’97, ’07, that means you). Consider it your reunion plan, already taken care of.

Browse & Plan Your Bids

Can’t attend the live auction but want to participate?

You can also bid by proxy—just reach out to Lisa Winick to be added to the list.

Browse Live Auction Items

What's New for Alumni

Curious what your fellow alumni have been up to lately?
Here’s a glimpse:

Ellie McMillen ’03 recently launched C & E Catering, a take-and-bake meal delivery company rooted in local, seasonal ingredients and thoughtfully sourced proteins. After years as executive chef at The Buttery (Millwood, VA)—and time spent living and traveling abroad—Ellie continues to bring people together around good food and shared tables.

If you’re local and looking to ease your nightly meal planning, her dishes are well worth a look.

Brandon Rutherford ’24, currently studying at Drexel University, was recently awarded the 2026 Photographic Society of America Scholarship, a national recognition of his work in wildlife and landscape photography. His work reflects a deep respect for natural environments—and last fall, he sold images to the National Zoo.

Follow Brandon's work

These are just a few of the updates being shared in Class Notes—a place for alumni to stay connected with each other and with Wakefield.

Have something to share? We’d love to include you.

READ the Latest Class Notes Share Yours

Reunion Years This Spring

Several classes are celebrating reunions this year—and it’s a great time to start thinking about how your class might come back together, whether this spring or at next year’s first Alumni Weekend.

Class of 2021 — 5th Reunion	Class of 1996 — 30th Reunion
Class of 2016 — 10th Reunion	Class of 1991 — 35th Reunion
Class of 2011 — 15th Reunion	Class of 1986 — 40th Reunion
Class of 2006 — 20th Reunion	Class of 1981 — 45th Reunion
Class of 2001 — 25th Reunion

Want to help bring your class back together?

Serve as a Reunion Rep—we’ll support you with outreach, planning, and logistics.

Be A Reunion Rep

Looking Ahead: Wakefield’s First Alumni Weekend

We’re already thinking ahead—and we want you to be part of it.

Alumni Milestone Weekend | April 30–May 1, 2027

will be Wakefield’s first-ever Alumni Weekend, welcoming all alumni back to campus for a spring celebration of connection and tradition. Join us for Field Day games (Alumni Spartan vs. Athenian tug-of-war, anyone?), a beer & wine social with your favorite teachers, reunions, Gold Cup, & more!

More details to come, but we hope you’ll save the date and plan to join us.

Stay Connected

Stay Connected with the Wakefield Alumni Network

Want to keep up with classmates and what’s happening at Wakefield? Join our alumni communities on Facebook and LinkedIn.

Follow on Facebook Join our LinkedIn

Update Your Contact Info

Make sure you’re on the list for events, spotlights, and invitations.

Update Us

Share a Class Note

We’d love to hear what life has brought your way. Share an update, milestone, or a favorite Wakefield memory to be included in our Alumni Class Notes.

Share with Us

Share Your WOD!

The Word of the Day was a Wakefield institution—120 formidable words that sharpened minds and shaped conversations.

Now we’re bringing it back in the Alumni Newsletter—long after most of us defenestrated our old WOD books.

What’s a WOD you still remember or use today?

Share your favorite, use it in a sentence, and tell us why it stuck with you:

Share Your WOD

Strengthening Leadership to Support Wakefield’s Growing Vision

Wed, 01 Apr 2026 04:00:00 +0000

Strengthening Leadership to Support Wakefield’s Growing Vision

We’re excited to share an important step forward at Wakefield School—one that strengthens how we support students across every stage of their journey.

As Wakefield continues to grow in both size and ambition, we are intentionally evolving our leadership structure to ensure that every part of the student experience—academic, social, and personal—is aligned, purposeful, and deeply connected.

A More Connected Vision for Student Growth

At Wakefield, a student’s experience is not defined by a single division or moment, but by the full arc of their journey—from their earliest years through graduation.

To support that vision, we are strengthening leadership across three key areas:

Academic Programs
Campus Life & Community Engagement
Alignment Across Divisions

Together, these areas ensure that what students experience at each stage builds meaningfully on what came before—and prepares them for what comes next.

Leadership Designed for Clarity and Impact

This updated structure brings greater coordination and focus to the work happening across our campus. Several key leadership appointments are central to this effort:

Head of Middle School
Keturah Maraska

We are so pleased to welcome Mrs. Keturah Maraska back as the Head of our Middle School. Keturah’s history with Wakefield School as a vital member of our teaching and leadership team, along with her deep connection as an alumni parent of Andrew ’18 and Joseph ’20, make her especially well-equipped for this critical role.

Keturah brings a unique lens to the Middle School as a critical “bridge” across divisions—supporting the alignment and elevation of our program from JK through Grade 12. The Middle School years represent a pivotal point in a student’s development, connecting the foundational experiences of the Lower School with the increasing independence and rigor of the Upper School. As such, this role plays a vital part in ensuring alignment of academic expectations, student growth, and community culture across the Wakefield journey.

Assistant Head of School for Academic Programs
Kerry Owen

Mrs. Kerry Owen will serve as the senior leader responsible for the cohesion and continued evolution of Wakefield’s JK–12 academic program. In this role, she will guide the delivery of our curriculum, support excellence in teaching and learning, and ensure that our academic offerings remain both distinctive and future-focused.

Kerry will continue to directly oversee our Lower School (JK–Grade 5), strengthening the foundational experiences that are so critical to a student’s long-term success. She will also serve as a key thought partner and coordinating leader for our Division Heads, helping to bring clarity, consistency, and shared purpose to our academic work across the school.

Working in close partnership with Head of Middle School Keturah Maraska and Head of Upper School Peter Findler, Kerry will help ensure that our academic vision is not only exceptionally well-designed but also coherent in practice across each stage of a Wakefield education.

Assistant Head of School for Campus Life & Community Engagement
Lisa Winick

Mrs. Lisa Winick will lead the development and coordination of the student and family experience beyond the classroom, ensuring that Wakefield’s culture, traditions, and programs are vibrant, inclusive, and deeply aligned with our mission. As an alumni parent of Kelsey ’16 and Dylan ’17 and a longstanding member of the Wakefield community, including more than 15 years of service in administration, she brings a well-informed and meaningful long-term perspective on the Wakefield experience.

Lisa's leadership will serve as a central hub for aligning athletics, arts, student activities, and the many shared experiences that define life on our campus. She will also continue to work closely with our Parents Association and play a central role in strengthening community engagement, including key events such as our annual Gala Auction.

Lisa brings a deep commitment to cultivating belonging, student voice, and meaningful connection—ensuring that every member of our community experiences Wakefield not just as a place of learning, but as a place of purpose and connection.

Director of Advancement & Strategic Partnerships
Will Nisbet

Rounding out our leadership appointments, we are delighted to welcome Mr. Will Nisbet to Wakefield as Director of Advancement & Strategic Partnerships.

Will brings nearly two decades of independent school leadership experience and a proven track record of advancing transformational philanthropy. Most recently, he helped lead a successful $20 million capital campaign at The Hill School, positioning institutions for long-term growth and impact.

At Wakefield, Will will partner closely with the advancement team, me, and our Board of Trustees to lead our fundraising efforts, deepen relationships with our community, expand leadership giving, and build the momentum needed to realize our Campus Master Plan.

This role represents an important strategic investment in Wakefield’s future. With Will’s leadership, we are strengthening our capacity for major gifts, alumni engagement, and meaningful partnerships—ensuring that our vision is not only compelling, but fully resourced and sustained over time.

Moving Forward with Purpose and Alignment

What makes this evolution especially meaningful is how these roles work together.

By strengthening alignment across academics, student life, and long-term strategy, Wakefield is building a more connected and intentional experience for every student—from their earliest years through graduation.

This structure allows the school to move forward with clarity and momentum, ensuring that each stage of the Wakefield journey is both purposeful in itself and part of something larger.

Ready to learn more about what makes Wakefield exceptional?
Visit our Admissions page

Wakefield Awarded National Grant to Advance Faculty Excellence

Tue, 17 Mar 2026 04:00:00 +0000

Wakefield Awarded National Grant to Advance Faculty Excellence

We’re proud to share meaningful national recognition at Wakefield School.

Wakefield School has been awarded a $100,000 grant from the Edward E. Ford Foundation—one of the most respected philanthropic organizations in independent education—recognizing schools that are shaping the future of teaching and learning.

National Recognition for Teaching Excellence

At Wakefield, excellence in teaching is intentional. Our educators take initiative, embrace growth, and continually pursue mastery in service of their students.

We are proud to share that Wakefield has been awarded a $100,000 grant from the Edward E. Ford Foundation, one of the most respected philanthropic organizations in independent education. This highly competitive national recognition is awarded to a small number of schools each year and reflects those poised to shape the future of teaching and learning both within their own communities and across the broader educational landscape.

Selected Among the Nation's Leading Schools

Selected as one of only 18 schools nationwide to receive the award this year, Wakefield is also among a select few schools to have earned two E.E. Ford grants within a four-year span. In fact, only two schools nationwide have received multiple Ford grants in the past five years — an extraordinary vote of confidence in Wakefield’s vision and the leadership of our faculty.

About the Edward E. Ford Foundation

Founded in 1957, the Edward E. Ford Foundation is dedicated to strengthening teaching and learning in independent schools. The Foundation supports initiatives that advance promising educational practices, elevate faculty leadership, and extend impact beyond a single campus.

The application process itself is highly selective and rigorous. Schools undergo a multi-stage vetting process, including an initial proposal, a detailed review with the Head of School, and an in-person campus visit, before being invited to apply. Grant awards range from $25,000 to $100,000, with Wakefield receiving the Foundation’s highest level of support.

Why Wakefield Was Selected

Wakefield’s award reflects the transformative potential of our Campus Master Plan and our deep commitment to faculty development.

It affirms our vision for a 60-acre campus that functions as a living laboratory where learning is experiential, interdisciplinary, and deeply connected to the world beyond the classroom. At its core, however, this recognition is rooted in something even more fundamental: our faculty and our commitment to preparing them for what education now demands.

Preparing Educators for What Comes Next

As the pace of change accelerates, shaped by emerging technologies, evolving disciplines, and global complexity, what it means to be educated continues to shift. To fully realize the promise of our evolving campus, we must invest in our teachers now so they are equipped to lead what comes next.

“By prioritizing our teachers today, we ensure our future campus fulfills its promise as a powerful engine for excellent teaching, deep learning, and meaningful engagement with the world,” said Wakefield Head of School Ashley Harper. “This recognition affirms our commitment to investing in teachers as the driving force behind an exceptional Wakefield education.”

In awarding this grant, the Edward E. Ford Foundation recognizes both Wakefield’s forward-thinking approach to education and the leadership of our faculty in shaping the future of teaching and learning.

Investing in the Educators Who Bring Learning to Life

The grant will fund professional learning grants and stipends for Wakefield faculty, supporting conferences, workshops, and advanced study that deepen expertise and strengthen instructional practice.

These opportunities will empower our teachers to:

Advance professional mastery and collaboration to sustain high-quality instruction
Lead place-driven learning that activates the full potential of our evolving campus
Launch mission-aligned programs and curricular innovation, including interdisciplinary and real-world learning experiences
Align with the Campus Master Plan, ensuring new spaces and ideas are activated with purpose and academic excellence

Importantly, this initiative will also establish a permanently endowed fund for faculty development, ensuring that this investment continues to support Wakefield educators and the students they serve for generations to come.

Unlocking a Transformational Investment

Like all E.E. Ford grants, this award is designed to multiply impact. Wakefield must raise a $100,000 community match, unlocking a total $200,000 investment in faculty development.

This effort will take center stage at our 30th Anniversary Gala Auction on Saturday, April 11, 2026, during Raise the Paddle—a signature moment when our community rallies behind a shared, mission-driven priority. This year, Raise the Paddle focuses on meeting this match and investing in the educators who bring Wakefield’s mission to life.

A Defining Commitment to Wakefield’s Future

This grant represents more than recognition. It is a call to action and a defining investment in Wakefield’s future.

As we look ahead, our focus is not simply on how our campus evolves, but on how it elevates teaching, deepens learning, and strengthens real-world connections. By supporting our educators today, we reinforce the foundation of what makes a Wakefield education distinctive.

We invite you to be part of this effort—whether at the Gala or online. Every gift brings us closer to unlocking this transformational opportunity for our faculty.

Support Raise the Paddle

Together, we can unlock this moment, empowering our educators and shaping the future of learning at Wakefield.

Ready to learn more about what makes Wakefield exceptional?
Visit our Admissions page

Scenes from School: I Was Shreked

Mon, 02 Mar 2026 05:00:00 +0000

Scenes from School: I Was Shreked

A Review of Wakefield's Production of Shrek The Musical

By Matt Zontine, Academic Dean & English Department Chair

From the set design to the choreography to the cast, the performance of Shrek was billed as “one of the biggest productions ever staged in the GLO” theater, according to Jonz.

This audience member was present for the final show, a matinee performance on Sunday, and the collection of adults and students bowing at its conclusion revealed the massive nature of the undertaking, as the stage was too small to accommodate the entire cast and crew. Whether they were treading the boards, behind the scenes, in the tech booth, sewing costumes, teaching dance moves and musical numbers, or directing the whole massive undertaking, there were simply too many people to individually credit in this brief review.

For the record, the playbill lists 35 student cast members and 23 student crew members. The four most prominent actors in the musical were Patrick R. (Shrek), Sydney W. (Fiona), Bryan B. (Donkey), and Lochlan P. (Lord Farquaad), but they were not the only thespians worth mentioning, by any means.

Summoning his inner ogre, Patrick’s performance was quite subtle, despite the facial prosthetics, Frankenstein monster shoes, and inclination to produce bodily noises. He captured both the character’s frustration with the outer world and a desire to be loved, with a nuanced mixture of sarcasm and longing.

Sydney’s princess gained steam as the play progressed. Her “damsel in distress” character evolved into a strong, determined foil to her swampy protagonist, and Sydney’s growling vocal inflections and dance moves during “I Think I Got You Beat” made me spontaneously chuckle.

Bryan played Shrek’s loyal companion with a mixture of physical comedy and hilarious befuddlement. My favorite moment was his number with the Dragonettes (Avery M., Olivia H., Kassidy M.), which was a tour de force of vocal talents, dance choreography, and set design.

Lochlan’s Lord Farquaad has to be seen to be fully appreciated. Cast as the smarmy, malevolent antagonist, the sophomore absorbed himself in the role, yet his sly winking at the audience, literal and metaphorical, also revealed something of the Lochlan we all know. His rendition of “The Ballad of Farquaad” nearly brought the house down.

Although there were many performances worth pointing out, I will conclude with those by Zach L., Savannah K., and Tee S. Zach was like a utility infielder who could play any position on the field. One moment, he was the captain of the guard, the next the bishop, and then, apparently, he was a puppeteer as well. Savannah was unrecognizable as Pinocchio (I had to check the program), and her voice was delightfully comical. Lastly, Tee’s performance as the Big Bad Wolf cannot go unmentioned. Although he appeared in ensemble numbers, I challenge any audience member to deny that their eyes were drawn to him wherever he was on the stage.

I apologize for not mentioning other stellar performances and work behind the scenes, but there is only so much time and space. If you saw one of the performances this weekend, fill in the blanks with your favorite moments. If you missed the shows, you do not know what you missed, and apparently, you do not know the Muffin Man either.

Artistic Director:  David Grimes
Music Director:  Lisa Newton
Choreography:  Corinne Johnson
Costume Design:  Jessica Lanham
Costume Assistant:  Christine Rosenfeld
Scenic Design:  Lochlan Prime '28
Lighting Design:  Tom Kennedy
Technical Director: Michael "Jonz" Jones
Theater Volunteer:  Erin Pieracci, Oksanna Hooper

A New Chapter for Wakefield Squash

Sun, 01 Mar 2026 05:00:00 +0000

A New Chapter for Wakefield Squash

By Zachary Mahevich '29

Published in: Country Zest & Style - Spring 2026, p. 21

Zack Mahevich is a freshman at Wakefield and a member of the varsity squash team.

Wakefield School, a JK–12 independent school in The Plains, Virginia, began the 2026 squash season with a new partnership with Bee Squash, a high-performance training program based at The St. James School in Springfield. This collaboration allows Wakefield students to continue receiving professional coaching, with Henry Beach stepping in as head coach.

Beach has been playing squash since childhood, reaching a top ranking of No. 7 in the junior division. Following his own successful junior squash career, he took an unconventional break from the sport to play bass guitar for the indie rock band Larkins.

He eventually returned to squash, rediscovering his passion for the game and developing a strong desire to help other young players succeed at the sport. Most recently, he competed in his first PSA Pro Match at the Bee Squash Expression Open.

Former Wakefield head coach Mark Broekman accepted a position as Assistant Coach at the University of Virginia after leading his 2025 team through a successful season and victory at the 2025 Division 6 National Finals in Philadelphia.

Following that championship run, the majority of the 2025 team graduated the following spring. Only two players, both sophomores, remained for the 2026 season, the new roster composed almost entirely of underclassmen. This year’s team advanced to the national tournament again, playing in Division 8 (two levels lower) and finished fifth.

Building a competitive squash team from a relatively inexperienced group was a major challenge, and Beach’s coaching and enthusiasm quickly earned the respect of all the players and drastically elevated each athlete’s level of play.

The two veteran sophomore players, Wyatt Wood and Nathan Torres, moved from being the youngest players near the bottom of the roster the prior year to this year’s No. 1 and No. 2 positions. Both took on roles as co-captains, demonstrating strong leadership and a deep interest in the improvement of every teammate.

“Coach Henry really filled the massive shoes of my old coach and built a team that had previously been filled with graduating seniors,” Wood said. “My expectations this year were low, but this team really surprised me with the chemistry and energy we had by the end of the season. I’m really excited for the future [of this] team and coach because I truly believe we will be the best team my school has seen.”

Wakefield students have the J.B. Rich Squash Center on campus and receive professional coaching during the squash season. This is a unique opportunity that has created many new squash enthusiasts each year.

Wakefield currently competes in both the Chase Interclub Varsity League (CIVL) and the Mid-Atlantic Squash Organization (MASO), alongside schools such as Woodberry Forest, the Potomac School, and Mercersburg Academy. All are much larger boarding schools that offer coached play throughout the academic year.

Wakefield’s smaller student body and relatively remote location have always created challenges for the team. However, the students’ love for the sport and fierce commitment beyond the season have kept it highly competitive and undeterred. Those challenges have also created an unbreakable sense of camaraderie and lasting friendships. With many years to come for this young team, they have great potential for more success.

From the Owl's Nest: Stories That Connect Us (Winter 2026)

Sun, 08 Feb 2026 05:00:00 +0000

From the Owl's Nest: Stories That Connect Us

Wakefield School Alumni Newsletter – Winter 2026

This newsletter is designed to reconnect our Alumni with Wakefield through stories, updates, and opportunities to engage—with fresh energy behind the work and big celebrations on the horizon.

As we move through the winter season, Wakefield feels especially alive with reflection and connection—students uncovering our history, alumni sharing their stories, and new opportunities to reconnect taking shape.

Here’s what’s been happening—and how you can be part of it.

Our Students Want to Hear From You

Take a short survey created by Wakefield students

This winter, Wakefield launched J-Term for the first time—a two-week experience that invited students in grades 8–12 to step away from their regular coursework and explore new passions through focused, project-based learning.

Students explored everything from veterinary science and robotics to filmmaking, ethics, personal finance, and Wakefield’s own history.

One of those courses, Making a Wakefield Documentary with Mr. Watters, brought together students to research and reflect on Wakefield’s history. They explored archival materials, scanned historic photos, and began shaping a narrative of the school’s journey from its earliest days to the present. The students’ work comes at a meaningful moment, as Wakefield prepares to celebrate 30 years on the hill and plan its first Founders' Day next year.

What quickly became clear was how much they wanted to hear directly from alumni.

The idea to survey graduates came from the students themselves, who were eager to learn which teachers, traditions, and moments shaped your Wakefield experience—and how those experiences continue to matter years later. Your reflections will directly shape their work and help ensure Wakefield’s story is remembered and carried forward.

Share your Wakefield story with our student historians.

Take the Alumni Survey

Wakefield 2024–2025 Annual Report: A Look Back—and Forward

We’re pleased to share Wakefield School’s 2024–2025 Annual Report, now available to read online.

This year’s report includes a special two-part feature that many alumni will find deeply familiar, reflecting on where Wakefield has been—and where it is headed—as we approach 30 years on the hill.

In "The Leap That Built Us," longtime English teacher and beloved Wakefield presence Tutt Stapp-McKiernan revisits the school’s final year in the nursing home and the extraordinary trust our community placed in Wakefield during that pivotal time. Alumni will recognize not only her voice, but the spirit of the school she so clearly captures—one shaped by resilience, belief, and a shared leap of faith that carried Wakefield forward.

In "Rooted in Place, Reaching Forward," Head of School Ashley Harper looks ahead to the next chapter, exploring how Wakefield’s land, mission, and programs continue to shape the school’s future as we prepare for that next leap.

Read the Annual Report

Head of School Ashley Harper Visiting West Coast Alumni this Month

Head of School Ashley Harper will be traveling to the West Coast later this month and would love to connect with Wakefield Alumni while she’s there.

San Francisco area: February 22–23

Seattle area: February 24–25

If you live nearby and would like to meet up—even informally—we’d love to hear from you.

Connect with Ashley

And if this is the first you’re hearing about the visit, it may mean we don’t have your current contact information.

Stay Connected

What's New for Alumni

Class Notes: Catch Up With Your Classmates

Have any exciting news to share?
Curious what your fellow alumni have been up to lately?

Our new Class Notes section is a place for alumni to stay connected—with each other and with Wakefield. Share milestones, moves, professional updates, family news, travels, or reflections you’d like your classmates to see. Then take a few minutes to browse and see what others are up to in life after the hill.

Whether you’re sharing or just catching up, Class Notes help keep the Wakefield alumni community connected—near and far.

READ the Latest Class Notes Share Yours

Reunion Years This Spring

Several classes are celebrating reunions this year! If you’re part of a reunion class and would like help organizing a gathering—or want to play a role in keeping your class connected—we’re here to support you.

Want to help bring your class back together?
We’re looking for Reunion Reps to serve as a point of connection for their class. That might mean helping keep classmates connected, sharing updates, or helping plan a reunion in whatever way feels right to you. We’ll support you with outreach, planning tools, and logistics.

Be A Reunion Rep

Class of 2021 — 5th Reunion	Class of 1996 — 30th Reunion
Class of 2016 — 10th Reunion	Class of 1991 — 35th Reunion
Class of 2011 — 15th Reunion	Class of 1986 — 40th Reunion
Class of 2006 — 20th Reunion	Class of 1981 — 45th Reunion
Class of 2001 — 25th Reunion	Class of 1976 — 50th Reunion

Looking Ahead: Wakefield’s First Alumni Weekend

We’re already thinking ahead—and we want you to be part of it.

Alumni Milestone Weekend | April 30–May 1, 2027

Community Corner

The Sparkling Speakeasy: Join Us for Wakefield’s 30th Anniversary Gala Auction

Step through the hidden door and into a night of sparkle, intrigue, and generosity.

Date: Saturday, April 11, 2026
Time: 6:30 PM
Location: GLO Theater, Wakefield School

Join us for The Sparkling Speakeasy, Wakefield School’s 30th Anniversary Gala Auction, on Saturday, April 11, 2026—an evening filled with hush-hush glamour, unforgettable moments, and a community that knows how to celebrate with purpose.

This milestone year marks both the 30th Gala Auction and Wakefield’s 30th year on the Hill. For three decades, this signature event has brought the Wakefield community together in support of the programs, experiences, and opportunities that define a Wakefield education.

Can’t attend in person? You can still be part of the fun.
Alumni will be able to bid online or via proxy before and during the event. If you’d like to participate remotely, email Lisa Winick to be added to the proxy bidding list.

Alumni are also invited to get involved by:

Donating an auction item or experience
Sponsoring the event or a portion of the evening
Purchasing tickets or a table to join us in person

Your support—whether online or in the room—helps fuel the opportunities and experiences that shape Wakefield students today and tomorrow.

Get Your Tix, Sponsor, or Donate

With gratitude to the many parents, alumni, and friends who have planned, supported, and stewarded the Wakefield Auction over the past 30 years.
Your creativity, dedication, and generosity have helped shape one of Wakefield’s most beloved traditions.

Enjoy a few auction throwbacks from years past.

Stay Connected

Follow the new Wakefield Alumni Facebook Page

Stay in touch, share updates, and see what your classmates are up to.

FOLLOW ALUMNI

Update Your Contact Info

Make sure you’re on the list for events, spotlights, and invitations.

Update Us

Send Us a Throwback Photo or Life Update

We’re building our 30th Anniversary archives and would love to include your Class Notes or memories.

Share with Us

Share Your WOD!

Share your favorite, use it in a sentence, and tell us why it stuck with you:

Share Your WOD

Scenes from School: It's Beginning to Look a lot like Saturnalia

Thu, 01 Jan 2026 05:00:00 +0000

Scenes from School: It's Beginning to Look a lot like Saturnalia

Inside a Latin class where history, humor, and holiday tradition collide in a celebration of the ancient world.

By Matt Zontine, Academic Dean & English Department Chair

The ancient Roman festival of Saturn in December, which was a period of general merrymaking.

Every December for the past three years, Mrs. Daeschel has been hosting a Saturnalia celebration with her Latin students. This Roman holiday, honoring the God of the Harvest’s release from his shackles, was a six-day party of feasting, decorating, and gift-giving (sound familiar?) that began on the 17th of the month.

Daeschel recognizes that the holiday is a bit strange in that it celebrates a god that is often perceived to be evil––he did eat his children after all. Throughout the year in Rome, a statue of Saturn was bound, but near the Winter solstice, the chains would be removed, symbolizing liberation and the start of a new year. In fact, part of her reasoning for hosting this Roman fete is to point out the “absurdity of the celebration and the releasing of this ambivalent god.”

The Latin classes participated in many of the same activities as their Roman ancestors. The students were provided with dice to create their own games of chance, and they received gifts of a candle and poetry. This year, the students wrote the poems in an intentionally poor manner and shared them with other Latin scholars. Mrs. Daeschel commented that it is a “day of role reversal where the slaves could wear the hats of the freedmen.” Thus, after winning the first dice game, junior Sydney W. became the saturnaliciusprinceps for the Latin IV class, earning a crown, a pile of popcorn, and being granted deejay privileges for the day.

Although the class I observed was atypical, Roman life plays a big part in Daeschel’s approach to Latin. She notes that the course needs to have a balance of language and culture, as the students “do not want to diagram sentences all day without meaning. You have to have meaning behind it for students to care.”

A typical class threads this needle. Mrs. Daeschel likes to start with grammar “while the students are fresh.” They worked together as a class or sometimes in smaller groups to translate texts. Next, they move on to history in the form of video, slides, or read a primary text in translation. Finally, they may write out a translation on their own or in pairs. Whatever the lesson, any observer walking by her classroom in the library will undoubtedly notice that the students are engaged and involved in the learning process.

In response to the $64,000 Question: Why do you teach Latin?, Daeschel was quick in her reply. She remarked, “In the practical sense, Latin is somewhat close to math. You are solving sentences. Understanding parts of speech, cases, etc. When students start to notice the repetition, they can solve the sentences. You have to look at the whole sentence before you make the words fit in. You have to look at the whole problem before you start.”

Moreover, she commented that “One of my favorite things about Latin is the culture. There are so many hot-button issues in the ancient world that also exist now. It gives a really safe space to talk about things that have a direct analogue to today, without people getting hurt. We get to approach these topics without a lot of baggage.”

Although my understanding of Latin is limited to what I have seen on U.S. currency or legal documents, Mrs. Daeschel certainly has convinced this reporter to support keeping this dead language alive.

Wakefield Thought Leaders

Curiosity, Meaning, and Service: Rachel Squire Munson ’06 Addresses the Class of 2026

Curiosity, Meaning, and Service

Rachel Squire Munson ’06 Addresses the Class of 2026

Each year, Wakefield welcomes a distinguished alumna or alumnus back to campus to address the graduating class at Commencement.

Read her full Commencement address below.

About the Speaker

Stay Connected

Stay Connected with the Wakefield Alumni Network

Update Your Contact Info

Share a Class Note

Scenes from School: "Words and Ideas Can Change the World"

Scenes from School: "Words and Ideas Can Change the World"

~ John Keating from Dead Poets Society

At the Junior Thesis Forum, students engage deeply with literature—crafting arguments, defending ideas, and discovering the power of their own voice.

By Matt Zontine, Academic Dean & English Department Chair

In the Spotlight: Wakefield’s The Play That Goes Wrong Featured in Middleburg Life

In the Spotlight: Wakefield's The Play That Goes Wrong Featured in Middleburg Life

This piece highlights the article published in Middleburg Life & Hunt Country (April 2026): “The Play That Goes Wrong”: Dr. Toby Brings the West End Hit to Wakefield By Diane Helentjaris

From the Owl's Nest: Familiar Faces Worth Celebrating (Spring 2026)

From the Owl's Nest: Familiar Faces Worth Celebrating

Wakefield School Alumni Newsletter – Spring 2026

This newsletter is designed to reconnect our Alumni with Wakefield through stories, updates, and opportunities to engage—with fresh energy behind the work and big celebrations on the horizon.

A (Very Quiet) Surprise for Mr. Genther

Help Us Celebrate His 40th Year at Wakefield

From the Class of ’06: A Voice for Commencement

Wakefield's 30th Anniversary Gala Auction Goes Online—Join From Anywhere

Bidding opens April 6 and closes April 11 at 7:30 PM

Can’t attend the live auction but want to participate?

What's New for Alumni

Curious what your fellow alumni have been up to lately? Here’s a glimpse:

These are just a few of the updates being shared in Class Notes—a place for alumni to stay connected with each other and with Wakefield. Have something to share? We’d love to include you.

Reunion Years This Spring

Want to help bring your class back together?

Looking Ahead: Wakefield’s First Alumni Weekend

Stay Connected

Stay Connected with the Wakefield Alumni Network

Update Your Contact Info

Share a Class Note

Share Your WOD!

Strengthening Leadership to Support Wakefield’s Growing Vision

Strengthening Leadership to Support Wakefield’s Growing Vision

We’re excited to share an important step forward at Wakefield School—one that strengthens how we support students across every stage of their journey.

A More Connected Vision for Student Growth

Leadership Designed for Clarity and Impact

Head of Middle School Keturah Maraska

Assistant Head of School for Academic Programs Kerry Owen

Assistant Head of School for Campus Life & Community Engagement Lisa Winick

Director of Advancement & Strategic Partnerships Will Nisbet

Moving Forward with Purpose and Alignment

Wakefield Awarded National Grant to Advance Faculty Excellence

Wakefield Awarded National Grant to Advance Faculty Excellence

National Recognition for Teaching Excellence

Selected Among the Nation's Leading Schools

About the Edward E. Ford Foundation

Why Wakefield Was Selected

Preparing Educators for What Comes Next

Investing in the Educators Who Bring Learning to Life

Unlocking a Transformational Investment

A Defining Commitment to Wakefield’s Future

Together, we can unlock this moment, empowering our educators and shaping the future of learning at Wakefield.

Scenes from School: I Was Shreked

Scenes from School: I Was Shreked

A Review of Wakefield's Production of Shrek The Musical

By Matt Zontine, Academic Dean & English Department Chair

From the set design to the choreography to the cast, the performance of Shrek was billed as “one of the biggest productions ever staged in the GLO” theater, according to Jonz.

A New Chapter for Wakefield Squash

A New Chapter for Wakefield Squash

By Zachary Mahevich '29

From the Owl's Nest: Stories That Connect Us (Winter 2026)

From the Owl's Nest: Stories That Connect Us

Wakefield School Alumni Newsletter – Winter 2026

This newsletter is designed to reconnect our Alumni with Wakefield through stories, updates, and opportunities to engage—with fresh energy behind the work and big celebrations on the horizon.

As we move through the winter season, Wakefield feels especially alive with reflection and connection—students uncovering our history, alumni sharing their stories, and new opportunities to reconnect taking shape. Here’s what’s been happening—and how you can be part of it.

Our Students Want to Hear From You

Take a short survey created by Wakefield students

Share your Wakefield story with our student historians.Take the Alumni Survey

Wakefield 2024–2025 Annual Report: A Look Back—and Forward

Head of School Ashley Harper Visiting West Coast Alumni this Month

What's New for Alumni

Scenes from School:
"Words and Ideas Can Change the World"

This piece highlights the article published in Middleburg Life & Hunt Country (April 2026):
“The Play That Goes Wrong”: Dr. Toby Brings the West End Hit to Wakefield
By Diane Helentjaris

Curious what your fellow alumni have been up to lately?
Here’s a glimpse:

These are just a few of the updates being shared in Class Notes—a place for alumni to stay connected with each other and with Wakefield.

Have something to share? We’d love to include you.

Head of Middle School
Keturah Maraska

Assistant Head of School for Academic Programs
Kerry Owen

Assistant Head of School for Campus Life & Community Engagement
Lisa Winick

Director of Advancement & Strategic Partnerships
Will Nisbet

As we move through the winter season, Wakefield feels especially alive with reflection and connection—students uncovering our history, alumni sharing their stories, and new opportunities to reconnect taking shape.

Here’s what’s been happening—and how you can be part of it.

Share your Wakefield story with our student historians.

Take the Alumni Survey