On a beautiful early September morning, more than one hundred students new to Proctor gathered in the Teddy Maloney '88 hockey rink. After attending New Student Registration Day the previous day, boarding students had just experienced sleeping away from home – some for the first time – while day students enjoyed a last night in their own beds. They began to gather in small groups, and the first hints of connection began to form – tentative conversations giving way to nervous laughter and shared anticipation. Each Wilderness Orientation group consists of six or seven new students alongside two faculty members and one returning student leader. Leaders imparted final reminders and helped new students make final adjustments to pack straps and ensure equal distribution of group food. After passing through a tunnel of clapping, cheering returning students and Orientation support team members -- as if being willed forward into the adventure ahead -- new students loaded their packs onto minibuses or joined a trail into Proctor's own Woodlands.
Earlier that morning, students reflected on the endeavor they were about to embark upon. Their emotions were raw and honest. Practical worries surfaced first: "I'm most nervous just sleeping out in the wilderness," one admitted, while others fretted about the "shower situation" and whether they could "carry my backpack." Yet alongside their anxieties, we witnessed genuine excitement. They were eager to meet new people, to swim in rivers, to do things they "usually wouldn't do." One student articulated what many seemed to sense: that this experience would "force us all to communicate well" and bring them "closer to create that family environment."
Since 1971, Proctor has understood something essential about building culture – immediately following registration day, Wilderness Orientation is the most effective way to start the school year and welcome new students into the Proctor community. This deliberate sequencing is designed not only to ease students in gradually but, more importantly, to establish from day one that challenge, when properly supported, becomes the foundation for growth. Communication and collaboration skills emerge naturally when digital distractions and external noise fade away.
Pulling off the logistical feat of Wilderness Orientation is never easy – coordinating food for over 100 students in the backcountry, managing transportation, and ensuring safety. This year's drought caused one Orientation “support” team member to haul water to Ragged Mountain to ensure an orientation group could follow their regularly scheduled route. Yet we persist because of the confluence of factors that make Wilderness Orientation uniquely powerful – establishing deep relationships with faculty and peers, the challenge of physical movement through varied terrain, developing appreciation for and commitment to stewarding the natural world, and the self-awareness that emerges from unstructured time with one's thoughts. Some of our new students already intuited why Proctor begins this way. Students become (at least a little bit) more comfortable being uncomfortable. As one student thoughtfully observed:
"What we take from here, we can take with us during school. It's an experience we can bond over."
The Wednesday Evening Shift
Wilderness Orientation this year stretched from Monday morning through Friday midday. One particular reflection captured the arc of the experience. This student, to put it mildly, did not enjoy the start of Wilderness Orientation whatsoever—the lack of technology, the heavy pack hikes, the awkwardness of being thrown together with six strangers. The first several days were challenging and likely marked by resistance and discomfort. However, they reflected, "by Wednesday evening in the camp, and all day Thursday, something changed.” Conversations began to flow more freely. People began to appreciate their beautiful surroundings – they began to laugh and enjoy themselves. This seismic shift represents the ultimate goal of the program. It emerges through countless small moments – helping each other across rivers, problem-solving together to tie a tarp overhang, trying new trail food, late-night conversations under the stars, and early morning wakeups to damp sleeping bags after an overnight rain. This observation aligns with what David Strayer, a cognitive psychologist at the University of Utah, termed "the 3 Day Effect" – a shift occurring between 40-72 hours in nature when working memory resets, mental chatter quiets, and is replaced by concerns like staying warm, cooking, and setting up camp. Cortisol drops, the Default Mode Network (our brain's rumination headquarters) quiets significantly, and our nervous systems shift from sympathetic arousal to parasympathetic restoration.
What began as circles of strangers in a hockey rink has become both a support network of peers and a foundation of confidence that new students can draw upon when necessary. As we transitioned into the intensity of boarding school life this week, we trust our new students carry forward what they learned in the wilderness -- relationship building, self-discovery through challenge, mental resets in nature, and the confidence to work through difficulty together.
As our Head of School, Amy Smucker, reflected on her own first Wilderness Orientation: "I had never carried a backpack up a mountain, and I did it... There's going to be moments that are hard and things that are scary, but that's how we're going to grow and that's how we're going to transform ourselves.” In a world that moves increasingly fast, that values digital connection over real-life connection, and that often shields young people from productive struggle, Wilderness Orientation stands as a counternarrative.
Read More about Wilderness Orientation and the Start of the Year
- Community and Relationships
- Environmental Stewardship
- Wilderness Orientation