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

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.

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!

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