Wakefield’s Senior Kayak Trip

A Tradition of Reflection, Unity, and Stewardship

By Elise Scalise

Published in: Warrenton Lifestyle Magazine - November 2025, p. 10 & Haymarket Gainesville Lifestyle Magazine - November 2025, p. 8

"The Senior Kayak Trip is far more than an outdoor excursion. It is a Wakefield tradition that strengthens bonds, celebrates friendship, and sets an intentional tone for the year ahead."

The launch of senior year at Wakefield School begins not in a classroom, but on the river. Each fall, the Senior Kayak Trip unfolds as a cherished rite of passage, weaving together personal reflection, class bonding, and environmental stewardship. This multi-day experience, steeped in tradition and meaning, sets the tone for the graduating class’s final year.

A Tradition with Intention and Heart

Far more than a class trip, the Senior Kayak experience is carefully and lovingly designed to meet students at this pivotal age and stage. As the student leaders of the school, seniors are invited to step deliberately into their roles, set individual and class goals, and reflect on the
connections and friendships that have shaped their growth.

This trip is also an intentional balance of beginnings and endings. As seniors embark on their final year, they begin the complex journey of stepping away from childhood and into young adulthood. The tradition itself, rooted in over two decades of partnerships with trusted outfitters and community partners, creates a web of care and resilience. Each year, the magic of the trip is renewed by the students themselves, whose openness and eagerness to connect elevate the
experience.

Adair Shanks ’25 reflected, “The senior kayaking trip was more than just an adventure on the
water. It began my journey as a senior, drawing me closer to classmates I’d grown up with and
offering time to reflect on our laughter and memories before paddling off toward whatever came
next.”

Evening of Reflection

The journey begins at Caroline Furnace, where students gather for an evening of writing and heartfelt connection. Each senior receives a 3x5 card for every classmate and is invited to record sincere thoughts and memories for each peer. What might sound simple often turns into hours of deep reflection; while some finish in an hour, the current Wakefield record is an astonishing five hours and twenty-five minutes. This quiet but powerful practice creates a lasting keepsake for every senior and nurtures empathy and gratitude within the group.

Lessons from the River

The second day takes the class to the Shenandoah River, where they paddle six scenic miles under the guidance of Mr. Mike, a seasoned river guide with two master’s degrees in environmental science and biology. As students navigate the gentle currents, Mr. Mike underscores the idea that “water is the blood of the earth,” weaving lessons on ecology and responsibility into the day’s adventure. “Being out on the water gave me a chance to reflect on our journey as seniors and to truly appreciate the memories we’ve made,” shared Duncan Shanks ’25. The river becomes both a classroom and a metaphor, reminding students of their duty to care
for each other and the natural world.

Heart-to-Heart Around the Campfire

That evening, the tradition deepens with a talking circle, led by Dr. Daryanani, Director of Student Services and Wellness. In the glow of a roaring campfire, each senior speaks from the heart, offering personal stories, reflections, and words of encouragement. The conversations, often lasting three or more hours, foster a profound sense of trust and unity. At the conclusion of the circle, students receive the folders filled with the notes written by their classmates, a tangible testament to friendship and shared history.

Closing with Care and Responsibility

The trip concludes with a visit to the Luray Rescue Zoo, where students learn about the importance of caring for creatures that have been abandoned or mistreated. This final stop reinforces the trip’s overarching themes: compassion, stewardship, and the interconnectedness of all living things.

A Lasting Impact

The Senior Kayak Trip is far more than an outdoor excursion. It is a Wakefield tradition that strengthens bonds, celebrates friendship, and sets an intentional tone for the year ahead. Students know that they will gather again for a closing talking circle at the end of the year, bookending their senior journey with shared reflection. First-time chaperones often describe the experience as game-changing, while alumni recall it as one of the most meaningful milestones of their school years.

Brandon Rutherford ’24 reflected on this impact:
“The senior kayak trip was definitely the most memorable trip I had at Wakefield. The activities themselves were fun, but what stood out most was the company. Even though we’d all known each other for years, the trip brought us closer together and created memories I’ll never forget. As a senior, I was working on opening myself up more to my classmates, and the kayak trip gave me the chance to do that even further. It also gave me time to reflect on my years at Wakefield and prepare myself for what’s ahead.”

As the seniors paddle forward, literally and figuratively, this treasured tradition ensures that their final chapter at Wakefield begins with gratitude, unity, and a lasting commitment to each other and to the world they will soon enter. It is a trip crafted with love, mindfulness, and developmentally informed planning, a journey that invites students to embrace stewardship and the joy of a shared experience.