St. Benedict’s Preparatory School: A Half-Century of Appalachian Trail Transformation

Published August 7, 2026, 01:05 PM

The relentless May heat mirrored the internal inferno of exhaustion, frustration, and an overwhelming desire for a different outcome burning in 15-year-old Lilliana Galo’s mind. It was 2025, and Galo, alongside seven classmates, was three nights into a five-day odyssey on the Appalachian Trail, a journey that would traverse a significant portion of New Jersey. They had conquered approximately nine miles that day, with one or two more miles stretching between them and the relative sanctuary of their campsite. Every fiber of her being ached, from the raw, pulverized soles of her feet to the throbbing collarbone she had fractured mere days before embarking on this rigorous expedition.

"Discipline," Galo whispered to herself, her focus narrowing to the simple, repetitive act of placing one foot in front of the other. "You got this." She drew a deep, fortifying breath as the long, undulating climb up one of Kittatinny Mountain’s many modest summits finally relented, plunging into a brief, welcome descent. A collective cheer erupted from the group. Galo, positioned at the rear of their straggling procession, looked up. Her bedraggled companions, clad in a motley assortment of hand-me-down boots and backpacks that evoked a vintage REI garage sale from the late 2000s, were linked arm-in-arm. They navigated the downhill slope with a shared rhythm of giggles and mutual support, two by two.

"None of us had done anything like this before, so we were absolutely dying," Galo recounted later, her voice still tinged with the memory of that arduous trek. "But instead of giving in and quitting, we’d chosen to literally and figuratively lean on one another for strength." In that moment, a profound realization settled upon Galo: this was the very essence of what her teachers, upperclassmen, and school alumni had been extolling for months. She found herself showering her friends with a torrent of praise and encouragement, a testament to the burgeoning bond within their group.

"I realized these girls had become like sisters to me, and I felt so much pride," Galo confessed. "Up to then, I wasn’t sure if we had it in us to finish the hike. But I realized that we’d been building up to this moment where it became crystal clear that, working together, we could accomplish whatever we set our minds out to achieve." This 55-mile pilgrimage was the culmination of a mandatory rite of passage for all first-year students at St. Benedict’s Preparatory School, a private academy in Newark, New Jersey. For over half a century, rising sophomores at this esteemed institution have undertaken the Appalachian Trail in late spring, engaging in a self-guided exercise designed to cultivate leadership and foster team-building skills.

The program meticulously divides classes of approximately 190 students into smaller cohorts. These groups then embark on staggered hiking and camping expeditions along the AT. Within each team, students assume distinct roles—navigator, cook, medic, or captain—necessitating a profound reliance on one another for collective success. Mobile phones and other electronic devices are strictly prohibited, fostering an environment of present-moment engagement. While two faculty members, administrators, or upper-division students accompany each group to provide emergency support, their role is strictly supervisory; they do not participate in decision-making or offer assistance beyond moral encouragement. Significantly, the vast majority of students enter this program with little to no prior backpacking experience. For many, their exposure to the wilderness is minimal, if not entirely absent, prior to this immersive challenge.

Glenn Cassidy, the current program director, a proud alumnus of Benedict’s Class of 1990, emphasizes that the experience is intentionally crafted to dislodge students from their urban comfort zones, introduce them to the enduring benefits of nature, and present an immersive challenge that demands collective effort for resolution. The overarching objective is to cultivate resilience, self-confidence, and a profound appreciation for the synergy of a team operating in perfect synchronicity. Moreover, the Appalachian Trail hike serves as a formal induction into the broader St. Benedict’s community. "When you cross that finish line, you’re following in the footsteps of every St. Benedict’s man and woman that’s come before you," Galo articulated. "The entire year has built to this point where you’ve proven to yourself and everyone else that you belong here and have what it takes to continue that lineage of success."

50 Years on the Appalachian Trail: An Accidental Genesis

Cassidy proudly asserts that the full-class program is unparalleled in the nation, its origins dating back to an accidental discovery in 1973. St. Benedict’s predecessor institution, established in 1868, served a predominantly working-class demographic composed largely of German, Irish, and Italian Catholic immigrants for approximately a century. However, a period of significant societal upheaval, including white flight and the aftermath of the 1967 Newark race riots, led to the closure of the predominantly Caucasian school in 1972. A determined cadre of monks subsequently reformed and reopened a more modest iteration of the institution a year later.

The foundational mission to educate underserved populations persisted, but the socio-economic landscape had dramatically shifted. Newark had emerged as a focal point of urban poverty, with nearly 60 percent of its residents residing in federally designated low-income areas by 1980. The relaunched school welcomed a student body that was almost exclusively comprised of Black and brown individuals. The new administration proactively implemented scholarships and comprehensive financial aid packages to ensure accessibility and affordability.

Cassidy explains that the school’s founders recognized that dismantling the entrenched cycle of poverty necessitated deep educational engagement. Experiential learning was thus elevated to a cornerstone of the curriculum. Administrators initiated an annual spring project, wherein students would segment into small groups and immerse themselves in subjects aligned with their professional interests. Specialized teams were formed for disciplines such as architecture, photography, art, and medicine, among others.

It was in 1973 that the founding headmaster, Edwin Leahy, conceived of a truly innovative endeavor: to lead students on an extended trek along the Appalachian Trail. He envisioned that a prolonged immersion in nature could foster a sense of quietude and cultivate nature-based self-regulation. Furthermore, the rigorous trial of a 50-plus-mile backpacking adventure was intended to instill invaluable virtues such as discipline, teamwork, and perseverance. The journey would also provide a conducive environment for profound discussions, ranging from emotional regulation and navigating personal challenges to exploring aspirations and future career paths.

"Problem was, Father Ed had never been backpacking," Cassidy disclosed. "Not only that, there was no gear or any discretionary funds to purchase it—and even if they’d had the money, no one would have known what to buy." Undeterred, Leahy harbored a profound conviction that the trek held the potential to fundamentally alter the trajectories of the young men’s lives. (St. Benedict’s transitioned to a co-educational institution in 2017 through a merger with a neighboring school.) He diligently procured maps and guidebooks and implemented a rigorous training regimen. Students engaged in physical conditioning exercises, including walking the school grounds with weighted backpacks and collaboratively navigating a makeshift obstacle course while blindfolded. This preparatory phase culminated in a practice hike to a nearby town.

The group, equipped with their sneakers and school backpacks filled with provisions and water jugs, embarked on a challenging 20-mile road walk. "They were so inexperienced that it took forever," Cassidy recalled. "Then they arrive after dark and realize: ‘How the heck are we gonna get back?’ Father Ed had to knock on the door of a monastery and ask to use their phone to call a ride." The inaugural AT trip was similarly marked by a series of unexpected misadventures. One student arrived with his mother’s rolling suitcase, while another had precariously lashed a set of cast-iron pans to his shoulder straps. Appropriate footwear was a foreign concept, and their sustenance largely consisted of peanut butter and jelly sandwiches. The absence of a support team and the non-existence of cell phones rendered the hike a true "make it or break it" proposition.

At one point, a student abruptly halted his progress, plunking himself down in the middle of the trail and refusing to continue. Leahy’s response was direct: "Fine, we’ll see you next year—in the event you can survive that long." Fortunately, this stern remark served as a powerful motivator, compelling the student to resume his journey. "But Father Ed told me later it was a miracle that they all survived," Cassidy admitted. Despite the initial chaos, the program demonstrated undeniable promise. The shared hardships of the quest forged an unbreakable bond between the boys and the headmaster, and they returned to the school as triumphant heroes. The mutual respect and camaraderie cultivated on the trail significantly aided their integration into the Benedict’s community, and behavioral issues among the students promptly abated.

The Program Evolves: A Legacy of Leadership and Resilience

The resounding success of the initial trek inspired Leahy to formalize the annual expedition. This pivotal mission received a significant impetus two years later when a new teacher, Mark Payne, a passionate outdoorsman and accomplished Scoutmaster with extensive backpacking expertise, volunteered to assume leadership of the nascent program. Payne recognized the profound transformative potential of the AT trek for both the students and the school. He understood that its efficacy hinged on both its scope and its structured implementation.

The subsequent overhaul of the program drew inspiration from a blend of Boy Scout protocols, conservation principles, and the deeply ingrained school values, epitomized by mottos such as, "Whatever hurts my brother, hurts me." Payne expanded the experience to encompass all first-year students, integrating it into a comprehensive year-long curriculum designed to cultivate a robust sense of school identity and belonging. "When you sign up to go to Benedict’s, you know about the hike," Galo stated. Her older siblings, who had attended the school, regaled her with legendary tales of their own backpacking adventures. "But you also understand it’s not this standalone thing, but more like a test that you slowly build up the confidence to know you can pass."

By the time Cassidy and his classmate Herb Brooks embarked on their AT hike in the late 1980s, the program had evolved into a highly refined and efficient operation. The preparations commenced in February with monthly, three-hour seminars that extended through April. These sessions provided comprehensive instruction in essential trail skills, including basic first aid, effective tick management, tent setup, outdoor cooking techniques, water purification, and map reading. A dedicated leadership class utilized case studies and reflective exercises to hone critical skills such as communication, team motivation, and sound decision-making.

Physical training began a month prior to Labor Day, starting with fundamental exercises like push-ups, sit-ups, and sustained jogging. The regimen progressively escalated to more complex activities, such as attempting to traverse a field using a pair of oversized skis with half the team facing forward and the other half backward—with some members blindfolded. Competitive elements, including obstacle course relay races, were incorporated, requiring platoons to strategically position teammates based on their individual strengths and weaknesses. This was followed by an overnight trial hike in Stokes State Forest, where groups practiced navigation by locating a series of checkpoints, manned by upper-level students, which guided them to their campsite. The subsequent week involved a thorough debriefing, analyzing both successes and challenges, and incorporating supplemental training to address any identified problem areas.

"After all of that, whatever anxiety I had about the trail had pretty much vanished," shared Brooks, now 53. "I looked forward to it as a grand adventure and felt incredibly privileged to have the opportunity to do something that, at that time in my life, I wouldn’t have had access to otherwise."

Hiking into the Future: Enduring Impact and New Beginnings

Both Brooks and Cassidy attest to the life-altering impact of their St. Benedict’s backpacking expeditions. For Cassidy, witnessing his teammates overcome personal doubts and collaboratively achieve a goal that some had deemed insurmountable was a profoundly moving experience. He actively volunteered with the program as an upperclassman and continued to contribute while pursuing his college education. These transformative treks ultimately inspired him to accept a position as athletics director and assistant to Payne in 1994.

"There’s something magical that happens out there," Cassidy remarked, now 54. He assumed the role of program director in 2007 and has since guided approximately 7,000 students. "The experience teaches kids important lessons about who they are, the world, their place in it, and the value of friendship." He elaborated that many students have never ventured beyond the confines of the city, let alone experienced the awe of gazing at the stars from a mountaintop. The opportunity to facilitate these formative experiences for young people became a profound calling.

Brooks’s professional trajectory followed a similarly inspired, albeit more circuitous, path. The AT trek ignited in him a lifelong passion for nature, wild spaces, and the profound sense of calm that envelops one during a forest walk. These hikes provided a crucial counterbalance to the inherent stresses of demanding roles within major New York City television networks and media companies. As 2020 approached, Brooks found himself increasingly reflecting on his formative experiences at St. Benedict’s.

"I realized I wanted to reshape my life around being outside and helping kids in urban areas access outdoor recreation opportunities," he stated. His volunteer work with organizations such as Outdoor Afro led to advanced training certifications and ultimately to a position as an adventure and course facilitator with the New York City Outward Bound Schools. "It’s such a full-circle thing for me to be doing," Brooks enthused. "But I can tell you, I’ve never gone to bed at night feeling so content—and I almost certainly wouldn’t have gotten here without St. Benedict’s."

Galo, now a second-year student, harbors equally profound sentiments about her transformative hike. Her background as a dedicated volleyball player and athlete had instilled a strong sense of confidence in her ability to meet the physical demands of the trek. She initially envisioned herself as the strong one, capable of carrying heavier loads for exhausted classmates and offering them unwavering support. The unexpected broken collarbone, however, dramatically reshaped those expectations. She was relegated to carrying a significantly lighter pack and found herself unable to perform basic tasks like tying her boots or setting up her tent. Her friends, without hesitation, readily stepped in to cover her responsibilities.

"At first, I felt useless and struggled with what my role should be," Galo admitted. "Then I realized that I needed to learn how to accept help and felt so much gratitude that my sisters were so gracious about giving it to me. It dawned on me that, while I couldn’t pitch in physically, I could pick them up mentally." Galo subsequently embraced the role of chief cheerleader for her team. She would hike alongside friends whose spirits began to flag, gently reminding them of their progress and the personal growth they had achieved. During breaks, she would lead impromptu pep talks and encourage the group to pause and appreciate the simple beauties of their surroundings—the melodic gurgle of a nearby creek or the breathtaking expanse of a 2,000-foot vista.

Galo’s experience on the Appalachian Trail was so overwhelmingly positive that she has since become a dedicated mentor for incoming first-year students, volunteering her time to assist with the current year’s hike. Furthermore, she participated in a summer outdoor learning initiative at Grand Teton National Park. "Being on the trail showed me there was more to life than being in a city, and how to see past all the busyness and noise," Galo reflected. While her future plans remain fluid, one certainty has emerged: she is committed to dedicating ample time to the pursuit of nature, mountain adventures, and backpacking.