A 50-Year Legacy: St. Benedict’s Preparatory School’s Appalachian Trail Trek Forges Resilience and Brotherhood

Published August 7, 2026, 01:05 PM. The uncharacteristic May heat of 2025 did little to alleviate the internal inferno burning through 15-year-old Lilliana Galo’s mind: fatigue, frustration, and a longing for it all to end. For three nights, she and seven classmates had been immersed in a five-day odyssey on the Appalachian Trail, a journey that would traverse a significant portion of New Jersey. Each day presented a grueling nine miles, with one or two more looming before the day’s camp. Every inch of Galo’s body screamed in protest, from the battered soles of her feet to a throbbing collarbone, a memento from a fracture sustained mere days before the expedition commenced. Yet, a mantra echoed in her thoughts: "Discipline. You got this." Her focus narrowed to her feet, ensuring they didn’t drag, one deliberate step following another. A deep breath filled her lungs as the long, arduous climb up a series of the Kittatinny Mountain ridge’s characteristic knobs finally leveled out, only to plunge into a brief, welcome descent. A cheer erupted from the group. Galo, positioned at the rear, looked up. Her companions, clad in an eclectic mix of hand-me-down boots and packs, resembled a tableau straight out of a vintage REI garage sale advertisement. They were linked arm-in-arm, their laughter and mutual support a visible testament to their shared struggle as they navigated the downhill terrain.

"None of us had done anything like this before, so we were absolutely dying," Galo confessed later. "But instead of giving in and quitting, we’d chosen to literally and figuratively lean on one another for strength." This, she realized, was the very essence of what teachers, upperclassmen, and alumni had spoken of with such reverence throughout the year. Galo found herself showering her friends with praise and encouragement. "I realized these girls had become like sisters to me, and I felt so much pride," she shared. "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 trek represented the culmination of a mandatory rite of passage for first-year students at St. Benedict’s Preparatory School, a distinguished private academy in Newark, New Jersey. For over half a century, the tradition has seen rising sophomores embark on the Appalachian Trail in late spring, engaging in a self-guided exercise designed to cultivate leadership and foster team-building. The school’s cohorts, typically comprising around 190 students, are meticulously divided into smaller groups. These units then undertake the hike and camping in staggered intervals along the trail. Within each group, specific roles are assigned—navigator, cook, medic, captain—necessitating a profound reliance on one another for collective success. The modern technological tether is severed; phones and gadgets are strictly forbidden. While two faculty members, administrators, or upper-division students accompany each group to provide emergency support, their role is strictly observational, offering no direct assistance with decision-making or practical guidance beyond moral encouragement. Adding to the challenge, the vast majority of these students arrive with little to no prior backpacking experience, having spent minimal time, if any, in the wilderness, let alone the backcountry.

Glenn Cassidy, the current program director and a proud alumnus of Benedict’s graduating class of 1990, emphasizes the program’s core objective: to extract students from their urban comfort zones, introduce them to the enduring benefits of nature, and present them with an immersive challenge that demands collaborative effort. The ultimate aim is to cultivate resilience, bolster self-confidence, and instill a deep appreciation for the synergistic power of a team operating in unison. The Appalachian Trail hike also 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 stated. "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 stands as a unique initiative of its kind nationwide, its origins in 1973 being, by his account, a happy accident. The precursor to St. Benedict’s Preparatory School, founded in 1868, had long served a working-class community primarily composed of German, Irish, and Italian Catholic immigrants for approximately a century. However, a period of significant societal upheaval, marked by white flight and the profound impact of the Newark race riots of 1967, led to the closure of the predominantly Caucasian institution in 1972. A small, dedicated group of monks undertook the monumental task of reforming and reopening a more streamlined version of the school a year later.

The foundational mission of educating underserved populations remained, but the socio-economic landscape of Newark had dramatically shifted. By 1980, the city was grappling with one of the nation’s highest concentrations of urban poverty, with nearly 60 percent of its residents residing in federally designated low-income areas. The relaunched school welcomed a student body that was almost exclusively Black and brown. The new administration, recognizing the systemic barriers to opportunity, implemented robust scholarship programs and generous financial aid packages to make tuition accessible. Cassidy elaborates that the founders keenly understood that breaking the entrenched cycle of poverty necessitated a deeply engaging educational approach. Experiential learning was thus woven into the fabric of the curriculum. Administrators introduced an annual spring project where students, divided into small teams, would immerse themselves in subjects aligned with their professional interests. These specializations ranged across fields such as architecture, photography, art, and medicine.

It was in 1973 that the founding headmaster, Edwin Leahy, conceived of a truly novel idea: what if students were taken on a multi-day hike along the Appalachian Trail? He envisioned this wilderness immersion as a powerful catalyst for instilling quietude and fostering nature-based self-regulation. The rigors of a 50-plus-mile backpacking adventure, he believed, would powerfully impress upon young minds crucial values like discipline, teamwork, and perseverance. Furthermore, the extended journey would provide ample opportunity for profound conversations, addressing everything from emotional regulation and life challenges to personal aspirations and potential career paths. "Problem was, Father Ed had never been backpacking," Cassidy recalls with a chuckle. "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 by these logistical hurdles, Leahy remained steadfast in his conviction that the trek held the potential to fundamentally alter the life trajectories of these young men. (It’s important to note that St. Benedict’s embraced coeducation in 2017 through a merger with a neighboring school.) He meticulously acquired maps and relevant literature, and initiated a rigorous training regimen. Students engaged in strenuous physical conditioning, 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 neighboring town. The group, outfitted in their sneakers and school backpacks brimming with snacks and water jugs, embarked on a challenging 20-mile road walk. "They were so inexperienced that it took forever," Cassidy recounts. "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 Appalachian Trail trip proved to be equally steeped in misadventure. One student arrived with his mother’s rolling suitcase, while another had ingeniously (or perhaps disastrously) secured a set of cast-iron pans to his shoulder straps. Appropriate footwear was non-existent, diets were largely confined to peanut butter and jelly sandwiches, and tents were sourced from mass-market retailers. Without a dedicated support team and in an era preceding widespread mobile phone usage, the hike became a true test of make-or-break resilience. At one point, a student, utterly overwhelmed, declared he would go no further, planting himself squarely in the middle of the trail. Leahy’s response was stark: fine, they would see him next year, assuming he could survive that long. Fortunately, this seemingly harsh remark served as a powerful motivator, prompting the student to rejoin the group. "But Father Ed told me later it was a miracle that they all survived," Cassidy admits.

Despite the chaotic beginnings, the program demonstrated undeniable promise. The shared hardships of the quest forged a profound bond between the boys and their headmaster, and amongst themselves. They returned to the school as if they had conquered worlds. The mutual respect and burgeoning camaraderie were instrumental in their successful integration into the St. Benedict’s community, and a noticeable decrease in behavioral issues soon followed.

The Program Evolves: From Accidental Adventure to Institutionalized Excellence

The undeniable success of the initial foray inspired Leahy to formalize the annual trip into an institutionalized component of the school’s curriculum. This mission received a significant boost two years later when a new teacher, Mark Payne, a passionate outdoorsman and seasoned Scoutmaster with extensive backpacking expertise, volunteered to assume leadership of the nascent program. Payne firmly believed that the pioneering Appalachian Trail trek held transformative potential for both the students and the school as a whole. However, its true potency, he understood, hinged on a well-defined scope and a structured approach.

This comprehensive overhaul drew inspiration from a blend of Boy Scout protocols, conservation principles, and the deeply ingrained school values, eloquently encapsulated in mottos such as, "Whatever hurts my brother, hurts me." Payne strategically expanded the experience to encompass all first-year students and integrated it into a broader, year-long agenda meticulously designed to cultivate a strong sense of school identity and belonging. "When you sign up to go to Benedict’s, you know about the hike," Galo affirms. Her older siblings had attended the school, and their tales of backpacking expeditions were legendary. "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 efficient and well-oiled machine. The preparation 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 the art of map reading. A dedicated leadership class utilized case studies and reflective exercises to hone critical skills such as communication, team motivation, and strategic decision-making.

Physical training commenced a month prior to Labor Day. The regimen began with foundational exercises like push-ups, sit-ups, and extended jogging. It progressively advanced to more complex challenges, 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 were also incorporated, including obstacle course relay races where platoons were tasked with strategically positioning teammates based on their individual strengths and weaknesses. This was followed by an overnight trial hike in Stokes State Forest. During this excursion, groups practiced navigation skills by locating a series of checkpoints, manned by upper-level students, that guided them to their designated campsite. The subsequent week involved a thorough review of the trial hike, analyzing both successes and areas for improvement, and included supplemental training to address identified problem areas. "After all of that, whatever anxiety I had about the trail had pretty much vanished," shares 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: Lasting Impact and Evolving Roles

Brooks and Cassidy both attest that their St. Benedict’s backpacking trips profoundly altered the course of their lives. For Cassidy, witnessing his teammates overcome their individual self-doubts and collaborate to achieve a goal that many had initially deemed insurmountable was a deeply moving experience. He actively volunteered with the program as an upperclassman and continued his involvement 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," observes Cassidy, now 54. Having assumed the role of program director in 2007, he 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 states. For many students, the experience represents their first venture beyond the city limits, let alone the profound privilege of gazing at the stars from a mountaintop. Guiding young people toward these transformative experiences has become his life’s calling.

Brooks’s career trajectory, while perhaps more circuitous, followed a similarly impactful path. The AT trek ignited a lifelong passion for nature, wild spaces, and the profound sense of tranquility that descends during a walk in the forest. These wilderness excursions provided a crucial counterbalance to the stresses of demanding roles with major New York City television networks and media companies. As 2020 approached, Brooks found himself increasingly reflecting on his formative years 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 explains. Through volunteer work with organizations like Outdoor Afro, he acquired training certifications and subsequently secured 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 expresses. "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 similarly deep emotions regarding her hiking experience. Her background as a dedicated volleyball player and athlete had instilled in her a strong confidence in her physical capabilities, leading her to believe she would be the one to support her exhausted classmates. However, the broken collarbone shattered these expectations. She was relegated to carrying a minimal pack and was unable to perform basic tasks like tying her own boots or setting up her tent. Her friends stepped in to fill the void. "At first, I felt useless and struggled with what my role should be," Galo admits. "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."

Consequently, Galo embraced the role of the team’s chief cheerleader. She walked alongside friends whose spirits had begun to flag, gently reminding them of their remarkable growth throughout the journey. She led motivational pep talks during breaks and encouraged the group to pause and appreciate the simple beauty of a babbling creek or a breathtaking 2,000-foot vista. Galo’s experience was so overwhelmingly positive that she subsequently became a mentor for incoming first-year students and volunteered to assist with the current year’s hike. She also participated in a summer outdoor learning experience 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 reflects. While her future plans remain fluid, one certainty has emerged: she intends to dedicate ample time to embracing nature, the mountains, and the profound rewards of backpacking.