Wilderness Orientation 2026: Nobody Hikes Alone

I met my group on Registration Day, and almost immediately we set out together. Within minutes, they were chatting, playing games, and singing. One student launched us into a game: "I'm going on a camping trip and I'm bringing..." It was the beginning of five days of games, songs, stories, questions, and seemingly endless conversation. They started talking as we walked away from school and, remarkably, didn't really stop until we pulled back onto campus.

 

At Proctor, deep and meaningful relationships sit at the heart of our culture. They are the gateway to so much of what we ask our students and adults to do: take risks, challenge themselves, care for one another, discover who they are, and accomplish things they might never have imagined doing alone. Perhaps nowhere do we teach that more intentionally than on Wilderness Orientation.
 

Orientation is fun, and it is difficult by design. As educators we talk a lot about pushing students outside their comfort zones. The phrase may have become a cliché, but at Proctor, it happens every day: in our classrooms, living far away from home, boarding a plane for an off-campus program, leaving a phone behind, performing on stage, or trying a new sport.

On our third day, our group hiked about six miles over some pretty unforgiving terrain. There were river crossings, slippery rocks, and seemingly endless stretches of mud that my co-leader, Lynne Bartlett, cheerfully referred to as "brownie batter." At one point, I slipped off a log and submerged my entire boot and sock in black, mucky mud. There was nothing to do but pull my foot out and keep walking.
 

There were falls, scraped legs, and the beginnings of blisters. At one river crossing, Lynne stood in the freezing water to help guide the rest of the group across slippery rocks. We pulled each other back to our feet, cheered each other on, shared our best snacks, and talked about our families, our old schools, and what we were excited and curious about at Proctor.

In our group journal that night, one student captured the day perfectly: "My bag was killing my back, but the Skittles evened it out."
 

Hard things are still hard when we do them together. A heavy pack still hurts, the rain still falls, and your feet still get wet. But when we realize that we are not alone in either the challenge or the joy, something changes. We lean on each other. We laugh. We share the Skittles. We pull each other out of the mud. 
 

On our final morning, as we eagerly waited for Karine Dumont, who was picking us up in the Proctor minibus, hopefully with a box of donuts in hand, I asked the group what they had learned about themselves over the previous five days.

A common theme emerged: they had learned they could do more than they thought they could. I could relate.

That discovery sits at the heart of what I hope every student and adult experiences at Proctor. No matter how accomplished you are when you arrive, there is more in you: more courage and curiosity, more resilience and capacity to care for the people around you, and more joy. 

As I begin my second year as Proctor's Head of School, I know there is a lot in store for all of us. There will be good days, hard days, unexpected days, and truly incredible ones. There will undoubtedly be some rain and a little mud.
 

Five days in the woods reminded me that the lesson of Orientation isn't simply that we can persevere through something challenging. It is that we can do more than we imagined when we do those hard things together.

That lesson is as important for me in my second year at Proctor as it is for a student beginning their first. I don't have to carry the pack alone. None of us does. I am ready to see how far we can go.

Read More from Head of School Amy Smucker