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Why We Hike: 52 Years of Wilderness Orientation

Scott Allenby

For the past 52 years, the first week of September at Proctor Academy has been synonymous with Wilderness Orientation. While last year’s Orientation program had to be altered due to COVID-19, Proctor’s 118 new students are set to head into the wilderness of the White Mountains for five days once again. The experience that awaits them - the vastness of the wilderness, the challenges of hiking high peaks, and the relationships forged with classmates and faculty leaders - will lay the foundation for their Proctor journey. 

Proctor Academy Wilderness Orientation

We often field questions from new families about what to expect on Wilderness Orientation. The excerpt below of John Greenleaf Whittier’s poem The White Mountains provides a glimpse into the views and scenery of Orientation: 

The White Mountains 

By John Greenleaf Whittier 

The sunset, with its bars of purple cloud,

Like a new heaven, shine upward from the lake

Of Winnipiseogee; and had felt

The sunrise breezes, midst the leafy isles

Which stoop their summer beauty to the lips

Of the bright waters. We had checked our steeds,

Silent with wonder, where the mountain wall

Is piled to heaven; and, through the narrow rift

Of the vast rocks, against whose rugged feet

Beats the mad torrent with perpetual roar,

Where noonday is as twilight, and the wind

Comes burdened with the everlasting moan

Of forests and of far-off waterfalls,

We had looked upward where the summer sky,

Tasselled with clouds light-woven by the sun,

Sprung its blue arch above the abutting crags

O’er-roofing the vast portal of the land.

Last year’s 50th Anniversary of Wilderness Orientation celebration was abridged due to COVID-19. While last year’s new students only were able to spend two days and one night in the wilderness, this year’s incoming class will have the full Wilderness Orientation experience that every Proctor student has enjoyed (or at least survived) since 1971. That which we learn by preparing for and spending time in the woods is not merely an outdoorsy activity to kick off the year, but rather a powerful grounding experience that centers us as we enter the beautiful chaos of an academic year at boarding school. 

It is the lessons of planning, preparing, and executing a Wilderness Orientation route that we carry into the school year. We must be prepared, learn to trust those around us, pace ourselves, appreciate the little steps it takes to climb a great peak, take care of one another, and know that we each play an important role in making sure our journey is a successful one. These are the lessons former Assistant Head of School Chris Norris, former Head of School David Fowler, and others brought to Proctor from their time with Outward Bound in the early 1970s. They saw the power of small group experiences, where each member was stepping well outside their comfort zone, and experimented with how to overlay this educational model on a traditional boarding school. Fifty-one years later, we continue to benefit from their foresight and willingness to commit wholeheartedly to a grand experiment in building community that we remain a part of today. We cannot wait to get back in the woods this fall and put these lessons into practice alongside our new students! 

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  • Experiential Learning
  • Wilderness Orientation