For the past 52 years, St. Benedict’s Preparatory School in Newark, New Jersey, has maintained one mandatory rite of passage for all freshmen: a five-day, 55-mile hike along the Appalachian Trail.

This tradition begins in early spring, when students at this private high school start training through exercise and team-building, in addition to learning a specialty. Next, the group is broken down into smaller units with a captain, camp specialist, navigators, cooks and medics.

Then, in May, rain or shine, comes the actual hike. While there is “some adult supervision,” according to St. Benedict’s Prep administrator Glenn Cassidy, the kids are meant to rely on what they’ve learned—and each other—to complete the journey.

“The only way we can get through this is if we work........

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