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.
 

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.

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