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

Published August 7, 2026, 01:05 PM. The uncharacteristic May heat seemed to amplify the endless hours, and the unprintable expletives that burned through 15-year-old Lilliana Galo’s mind: fatigue, frustration, and fudge. It was 2025, and Galo, along with seven classmates, was three nights into a five-day trek on the Appalachian Trail that would traverse a significant portion of New Jersey. They had covered approximately nine miles that day, with one or two more to go before reaching their campsite. Every muscle ached, from Galo’s pulverized soles to the throbbing collarbone she had fractured mere days before embarking on the expedition.

"Discipline," Galo reminded herself, "You got this." Her focus narrowed to her feet, ensuring they weren’t dragging. One step, then another. She inhaled deeply. The long, gradual ascent up one of the many small knobs along the Kittatinny Mountain ridge finally leveled out, only to plunge into a brief, steep descent. A collective cheer erupted from the group. Galo, positioned at the rear, looked up. Her bedraggled companions, sporting hand-me-down boots and packs that evoked a nostalgic image of a late-aughts REI garage sale, were linked arm-in-arm. Giggles punctuated their progress as they navigated the downhill terrain, two by two, supporting each other.

"None of us had done anything like this before, so we were absolutely dying," Galo recounted 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 precisely what teachers, upperclassmen, and school alumni had been discussing throughout the year. She showered her friends with praise and encouragement. "I realized these girls had become like sisters to me, and I felt so much pride," Galo 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."

The 55-mile trek represents the culmination of a mandatory rite of passage for first-year students at St. Benedict’s Preparatory School. For over half a century, rising sophomores at the private Newark, New Jersey, academy have undertaken this challenging journey on the Appalachian Trail in late spring. This self-guided leadership and team-building exercise is designed to forge resilience, instill a profound sense of camaraderie, and cultivate the skills necessary for navigating life’s inherent challenges.

Classes, typically comprising around 190 students, are divided into smaller groups. These cohorts embark on their hikes and camping expeditions in staggered intervals along the trail. Within each group, students assume distinct roles – navigator, cook, medic, or captain – and their collective success hinges entirely on their ability to rely on one another. The program strictly prohibits the use of phones and other electronic devices, fostering an environment of complete immersion and interpersonal connection. While two teachers, administrators, or upper-division students accompany each group to provide emergency support, their involvement is strictly limited to non-intervention in decision-making processes, offering only moral encouragement. Compounding the challenge, a significant majority of the students enter the program with little to no prior backpacking experience. Many have spent minimal time, if any, in the wilderness, let alone the backcountry.

Glenn Cassidy, the current program director, is a proud alumnus of Benedict’s, graduating in 1990. He articulates that the program’s core design is to intentionally dislodge students from their urban comfort zones, introduce them to the enduring and profound benefits of nature, and present an immersive challenge that can only be overcome through collective effort. The ultimate aim is to cultivate resilience, bolster self-confidence, and foster a deep appreciation for the potent synergy of a team working in perfect synchronicity. The Appalachian Trail hike also serves as a formal, unifying initiation into the broader St. Benedict’s school 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 emphasizes. "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."

Fifty Years on the Appalachian Trail: A Journey Forged in Adversity

Cassidy highlights that the full-class program stands as a unique initiative of its kind in the nation. Its inception in 1973, however, was almost serendipitous. The predecessor institution to St. Benedict’s was established in 1868, primarily serving a working-class community comprised largely of German, Irish, and Italian Catholic immigrants for approximately a century. A period of significant societal upheaval, marked by white flight and the aftermath of the Newark race riots of 1967, led to the closure of the predominantly Caucasian school in 1972. A dedicated contingent of monks, driven by a steadfast commitment to education, reformed and reopened a more streamlined version of the school a year later.

The foundational mission of educating underserved populations remained central, but the demographic and socioeconomic landscape had profoundly shifted. Newark had emerged as one of the nation’s epicenters of urban poverty, with nearly 60 percent of its residents residing in federally designated low-income areas by 1980. The relaunched school attracted a student body that was overwhelmingly composed of Black and brown youth. The new administration proactively implemented scholarships and comprehensive financial aid packages to ensure tuition remained accessible.

Cassidy explains that the founders recognized that breaking the systemic cycle of poverty necessitated deep and sustained educational engagement. Experiential learning was thus elevated to a cornerstone of the curriculum. Administrators initiated an annual spring project, wherein students were divided into small groups and immersed in subjects aligned with their professional interests. These exploratory teams delved into fields such as architecture, photography, art, and medicine, providing hands-on exposure to diverse career paths.

It was in 1973 that the founding headmaster, Edwin Leahy, conceived of a truly novel approach: a multi-day hike along the Appalachian Trail. He envisioned that a prolonged immersion in nature could foster quiet contemplation and promote self-regulation through nature-based activities. This ambitious, 50-plus-mile backpacking adventure was intended to instill invaluable virtues such as discipline, teamwork, and unwavering perseverance. Moreover, the extended period in the wilderness offered a unique opportunity for candid discussions on a wide spectrum of topics, ranging from managing difficult emotions and navigating family dynamics to articulating dreams and exploring potential career aspirations.

"Problem was, Father Ed had never been backpacking," Cassidy recounts with a wry smile. "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 was convinced of the trek’s transformative potential for the young men’s life trajectories. St. Benedict’s embraced coeducation in 2017 following a merger with a neighboring school, broadening the program’s reach and impact. He meticulously acquired maps and consulted relevant literature, subsequently implementing 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 was followed by a practice hike to a nearby town.

The students laced up their sneakers, filled school backpacks with provisions and water jugs, and set off on a challenging 20-mile road walk. "They were so inexperienced that it took forever," Cassidy recalls. "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 was similarly marked by unforeseen challenges. One student arrived equipped with his mother’s rolling suitcase, while another had ingeniously, albeit inappropriately, secured a set of cast-iron pans to his shoulder straps. Footwear was woefully inadequate for the terrain, diets consisted predominantly of peanut butter and jelly sandwiches, and tents were sourced from discount department stores. Without a dedicated support team and in the absence of mobile phones, the hike was a true test of individual and collective mettle.

At one point, a student abruptly sat down in the middle of the trail, refusing to proceed. Leahy, employing a firm but calculated approach, informed him that they would see him the following year – assuming he could survive that long. Fortunately, this stark remark served as a potent 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 initial missteps and the sheer adversity, the program demonstrated undeniable promise. The shared hardships of the quest forged a profound bond between the boys and their headmaster, and they returned to the school as if they had conquered an epic challenge. The mutual respect and camaraderie that developed proved instrumental in their integration into the Benedict’s community, and a notable reduction in behavioral issues was promptly observed.

The Program Evolves: From Humble Beginnings to Institutionalized Tradition

The undeniable success of the initial trek inspired Leahy to formalize the annual trip into an institutionalized tradition. This mission received a significant boost two years later when a new teacher, Mark Payne, a passionate outdoorsman and experienced Scoutmaster, volunteered to assume leadership of the nascent program. Payne, a seasoned backpacker himself, firmly believed in the transformative power of the Appalachian Trail expedition for both the students and the school. He recognized that its ultimate potency was intrinsically linked to its scope and structured execution.

The subsequent overhaul of the program was informed by a blend of established Boy Scout protocols, core conservation principles, and the foundational school values, notably encapsulated in the motto, "Whatever hurts my brother, hurts me." Payne strategically expanded the experience to encompass all first-year students, integrating it into a comprehensive, year-long agenda meticulously designed to cultivate school identity and foster a profound sense of belonging. "When you sign up to go to Benedict’s, you know about the hike," states Galo. Her older siblings had attended the school, and their tales of backpacking adventures were the stuff of legend. "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 matured into a highly efficient and well-orchestrated operation. It commenced with monthly, three-hour seminars held from February 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 proficient use of topographical maps. A dedicated leadership class employed case studies and reflective exercises to hone crucial skills such as effective communication, team motivation, and sound decision-making under pressure.

Physical training commenced a month prior to Labor Day, initiating with fundamental exercises like push-ups, sit-ups, and extended jogging sessions. The regimen progressed 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 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, where groups practiced navigation by locating a series of checkpoints manned by upper-level students, which ultimately guided them to their campsite. The subsequent week involved a thorough review of the trial hike, analyzing both successes and shortcomings, and incorporating supplemental training for areas identified as needing improvement.

"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 Impacts and New Beginnings

Both Brooks and Cassidy attest that the St. Benedict’s backpacking trip served as a pivotal, life-altering experience. For Cassidy, witnessing his teammates surmount their self-imposed limitations and collaborate effectively to achieve a goal that many initially deemed impossible left an indelible mark on his psyche. He actively volunteered with the program as an upperclassman and continued his involvement during his college years. These transformative treks inspired him to accept a position as an athletics director and assistant to Payne in 1994. "There’s something magical that happens out there," remarks Cassidy, now 54. He assumed the role of program director in 2007 and has since guided approximately 7,000 students through the experience. "The experience teaches kids important lessons about who they are, the world, their place in it, and the value of friendship," Cassidy elaborates. For many urban students, the program represents their first exposure to the natural world beyond the confines of their city, offering them the awe-inspiring opportunity to gaze at the stars from a mountaintop. Assisting young people in encountering these profound experiences has evolved into a deeply fulfilling calling.

Brooks’s career trajectory followed a similarly inspired, albeit more circuitous, path. The AT trek ignited a lifelong passion for nature, wild spaces, and the profound sense of tranquility that envelops one during a walk in the forest. These hikes provided a vital counterbalance to the inherent stresses of demanding jobs with major New York City television networks and media companies. As 2020 approached, Brooks found himself increasingly reflecting on his formative experiences at Benedict’s. "I realized I wanted to reshape my life around being outside and helping kids in urban areas access outdoor recreation opportunities," he states. His subsequent engagement with organizations such as Outdoor Afro led to advanced training certifications and a position as an adventure and course facilitator with 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 equally profound sentiments about her hiking experience. Her background as a competitive volleyball player and athlete had instilled a confidence that she would be physically capable of meeting the demands of the trek. She initially envisioned herself as the one to carry extra gear for exhausted classmates, the strong support system they could lean on. However, the broken collarbone drastically altered these expectations. She was limited to carrying a minimal pack and found herself unable to tie her own boots or set up her tent. Her friends readily 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 chief cheerleader for her team. She walked alongside friends whose morale had begun to falter, reminding them of their personal growth and resilience. She initiated 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 proved so overwhelmingly positive that she has since become a mentor for incoming first-year students and has volunteered to assist with the current year’s hike. Furthermore, she participated in a summer outdoor learning program 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 career plans remain fluid, one certainty has emerged: she intends to dedicate significant time to experiencing nature, exploring mountains, and engaging in backpacking adventures.