From the Owl's Nest: A New Season of Connection

Wakefield School Alumni Newsletter – 2025

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.

Two Familiar Faces Leading Alumni Engagement

Wakefield is thrilled to share that Michele Lalonde Dudley ’08 and Kelsey Winick ’16 are expanding their roles on the Advancement Team to lead Alumni Engagement.

Both bring a deep love for Wakefield and a shared commitment to reconnecting, celebrating, and supporting our alumni community. As former students and now professionals on campus, they understand the traditions, relationships, and sense of purpose that make Wakefield what it is.

“Michele and Kelsey embody the heart of Wakefield—purposeful, passionate, and grounded in service,” said Ashley Harper, Head of School. “Their leadership will help our graduates rediscover the lifelong connections that make the Wakefield experience so special.”

Stay tuned for more ways to reconnect. The Wakefield Alumni Network is growing—and it’s in great hands.

30 Years on the Hill — Big Celebrations Ahead!

Next year marks 30 years since Wakefield moved to our campus in The Plains, and we’re celebrating in a big way.

Two new traditions will anchor our alumni calendar:

Founders Day — November 16, 2026
An annual celebration honoring the people and vision that began Wakefield’s chapter on this hill. Founders Day will be observed each year on the third Monday in November. 

Alumni Milestone Weekend — April 30–May 1, 2027
A spring tradition that brings all alumni back to campus the first weekend in May to reconnect, celebrate milestone reunions, and honor retirements. 

We’ve come a long way from our early days in the nursing home — and we can’t wait to celebrate the journey with you. We’ve got stories to tell and memories to relive.

Mark your calendars — more details coming in our Winter Alumni Newsletter.

Homecoming Highlights — Always a Spartan or Athenian

If you ever needed proof that the Spartan–Athenian spirit is still alive and well at Wakefield, you’d have found it at Homecoming this year.

The Homecoming Pep Rally kicked off our yearlong rivalry and began with our newest and youngest Owls officially welcomed into their Spartan and Athenian families. As the crowd cheered, first graders and new students ran through a tunnel of raised arms, high-fives, and smiles from their new teammates.

We also started the competition early this year with the Spartan–Athenian Buddy Games, and if you’re wondering, the Athenians took an early lead. We’ll have to wait until Field Day to see how it all shakes out.

The faces change, but as you know, that feeling of belonging — of finding your team — stays with you long after you leave the Hill.

Scenes from School: Robotics & Drones Take Off

Curious what Wakefield students are up to these days?

Check out this piece that Mr. Zontine (celebrating 25 years at Wakefield!) wrote about our Upper School Robotics & Drones course—a great glimpse into how far our programs have evolved.

While you’re reading, if you find yourself wondering what space those students are using—it’s our Dining Hall, which longtime Owls will remember as the original school library, where you could find Mrs. Burton organizing the stacks.

Who remembers getting out of class early to roll out tables and chairs to set up for lunch in the gym? Some things have changed, but teamwork clearly hasn’t.
 

READ MR. ZONTINE’S FULL STORY                             

Wakefield Giving Day — Alumni Torch $10K Match Challenge

Save the Date: Thursday, November 13 — it’s the 2nd Annual Wakefield Giving Day!

Wakefield Giving Day is a celebration of generosity, community, and school spirit that builds from now through Giving Day as the entire Wakefield family—alumni, parents, faculty, and friends—comes together to support the Wakefield Fund.

This year’s goal: $150,000 for the Wakefield Fund—fueling academics, arts, athletics, robotics, and real-world learning experiences.

And for alumni? A special challenge:
Every alumni gift will be matched dollar-for-dollar up to $10,000 thanks to a generous alum through the Alumni Torch Match Challenge.

Join your fellow alumni and double your impact — then show your Spartan or Athenian pride during the Power Hour Challenge at 11 AM to help put your team over the edge ahead of Field Day.

Let’s show what the alumni community can do.

Community Corner

An Invitation to Local Alumni Parents: Navigating Online Safety

Join us for an important conversation on Navigating Online Safety, presented in partnership with the FBI Washington Field Office.

Date: Wednesday, November 5
Time: 6:00 PM
Location: GLO Theater, Wakefield School

Children are connecting, playing, and learning online at younger ages than ever before. This session offers practical, expert guidance to help families stay informed and confident in today’s digital world.

RSVP below or share with others who may be interested—this event is open to the broader community.

Learn More & RSVP

From the Stage: Wakefield’s 2025–26 Theater Lineup

This season has something for everyone—from the icy wonder of Frozen Jr. to the larger-than-life fun

of Shrek the Musical and the chaos of The Play That Goes Wrong: High School Edition.

First up: Frozen Jr., this December!

Get Your Tickets Here!

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 pictures or stories.

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