St. Benedict’s Preparatory School: 50 Years of Appalachian Trail Transformation

Published August 7, 2026 01:05 PM

The hours seemed to have ground on forever, and F-words burned through 15-year-old Lilliana Galo’s brain like the uncharacteristic May heat: fatigue, frustration, and fudgggge! It was 2025, and Galo, along with seven of her classmates, were three nights into a five-day trek on the Appalachian Trail that would carry them through a significant portion of New Jersey. They had already logged approximately nine miles that day, with one or two more left to conquer before reaching their designated campsite. Every fiber of her being ached, from the pulverized soles of her feet to the throbbing collarbone she had broken just days before embarking on this demanding journey.

“Discipline,” Galo thought, her mind focusing with laser-like intensity. “You got this.” Her attention snapped to her feet, ensuring there was no dragging, just the rhythmic cadence of one step following another. She drew a deep, fortifying breath. The long, slow ascent up one of the many undulating knobs on the Kittatinny Mountain ridge eventually leveled out, only to plunge into a brief, welcome descent. A collective cheer erupted from the group. Galo, positioned at the rear of the pack, looked up. Her bedraggled friends, clad in hand-me-down boots and packs that evoked a nostalgic image from a late-aughts REI garage sale, were linked arm in arm, their laughter and support for one another evident as they navigated the downhill terrain.

“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 the very essence of what teachers, upperclassmen, and school alumni had been emphasizing 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,” Galo said. “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. For over half a century, rising sophomores at the private Newark, New Jersey, academy have undertaken this journey on the Appalachian Trail in late spring, engaging in a self-guided leadership and team-building exercise. Typically, classes comprising around 190 students are divided into smaller cohorts that hike and camp in staggered intervals along the trail. Within these groups, teammates assume distinct roles—such as navigator, cook, medic, or captain—and their success hinges entirely on their reliance on one another. The use of phones and electronic gadgets is strictly prohibited. While two faculty members, administrators, or upper-division students accompany each group to provide assistance in emergencies, their role is strictly supervisory, offering no direct help with decision-making or anything beyond moral support. Adding to the challenge, a significant majority of students enter this program with little to no prior backpacking experience, having spent minimal time in the wilderness, let alone the backcountry.

Glenn Cassidy, the current program director, a proud alumnus of Benedict’s from the graduating class of 1990, explains that the experience is meticulously designed to extract students from their urban comfort zones, introduce them to the enduring benefits of nature, and present an immersive challenge that cannot be overcome in isolation. The overarching goal is to cultivate resilience, foster self-confidence, and instill a profound appreciation for the power of a team working in perfect synchronicity. Beyond these immediate developmental objectives, the Appalachian Trail hike also serves as a formal initiation 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, underscoring the historical significance of the endeavor. “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

Cassidy proudly asserts that the full-class program is unparalleled in its uniqueness across the nation, and its genesis in 1973 was, in essence, an serendipitous occurrence. St. Benedict’s predecessor institution, established in 1868, served a working-class community predominantly composed of German, Irish, and Italian Catholic immigrants for approximately a century. A period marked by white flight and societal upheaval, particularly following the Newark race riots of 1967, led to the closure of the predominantly Caucasian school in 1972. However, a determined group of monks regrouped and reopened a more streamlined version of the school a year later.

The institution’s enduring mission to educate underserved populations remained central, but the socio-economic landscape had significantly shifted. Newark by 1980 was characterized by one of the nation’s highest concentrations of urban poverty, with nearly 60 percent of its residents living in federally designated low-income areas. The relaunched school welcomed a student body that was almost exclusively Black and brown, with the new administration implementing a robust system of scholarships and financial aid packages to ensure tuition accessibility. Cassidy emphasizes that the founders recognized that breaking the systemic cycle of poverty was intrinsically linked to deep educational engagement, with experiential learning playing a pivotal role in the curriculum. Consequently, administrators launched an annual spring project where students would be divided into small groups, immersing themselves in subjects of professional interest, with dedicated teams focusing on fields such as architecture, photography, art, and medicine.

It was in 1973 that the founding headmaster, Edwin Leahy, conceived a novel and ambitious plan: to lead students on a multi-day hike along the Appalachian Trail. He envisioned a prolonged journey through nature as a means to foster quiet contemplation and promote nature-based self-regulation. Moreover, the rigorous trial of a 50-plus-mile backpacking adventure was intended to instill core values such as discipline, teamwork, and perseverance. This immersive experience would also provide ample opportunity for meaningful dialogue on a wide range of topics, from managing difficult emotions and navigating family life to exploring personal dreams and potential career aspirations.

“Problem was, Father Ed had never been backpacking,” Cassidy revealed, highlighting the initial logistical hurdles. “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 challenges, Leahy remained steadfast in his belief that the trek held the profound potential to alter the life trajectories of these young men. (St. Benedict’s, it is worth noting, became a coeducational institution in 2017 following a merger with a neighboring school.) He meticulously procured maps and relevant literature and implemented a rigorous training regimen. Students engaged in physical conditioning, including activities like 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 with sneakers and school backpacks filled with snacks and water jugs, set out on a 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 Appalachian Trail trip was similarly marked by a series of unexpected challenges and misadventures. One student arrived equipped with his mother’s rolling luggage, while another had ingeniously, though imprudently, tied a set of cast-iron pans to his shoulder straps. Appropriate footwear was virtually non-existent; the prevailing diet consisted primarily of peanut butter and jelly sandwiches; and tents were sourced from discount big-box stores. With no established support team and the absence of cell phones, the hike was a true test of their mettle, a “make it or break it” scenario.

At one point, a student abruptly sat down in the middle of the trail, refusing to continue. Leahy, in a stern but strategic move, informed him that they would see him the following year—implying he might not survive the interim. Fortunately, this 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 recounted with a mixture of awe and relief. Despite the chaotic beginnings, the program demonstrated undeniable promise. The shared hardships of their quest fostered a deep bond between the boys and the headmaster, and they returned to the school as triumphant heroes. The mutual respect and camaraderie that emerged from the experience proved instrumental in their integration into the Benedict’s community, and a noticeable decline in behavioral issues followed promptly.

The Program Evolves

The undeniable success of the initial undertaking 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 fledgling program. Payne, an accomplished backpacker himself, firmly believed in the transformative potential of the Appalachian Trail trek for both the students and the school. He recognized, however, that its efficacy was contingent upon a more structured and comprehensive approach.

This strategic overhaul drew inspiration from a confluence of established Boy Scout protocols, core conservation principles, and the deeply ingrained school values, articulated in mottos such as, “Whatever hurts my brother, hurts me.” Payne expanded the scope of 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 explained, her older siblings having also attended the school and regaled her with legendary tales of their backpacking experiences. “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 own AT hike in the late 1980s, the program had evolved into a remarkably well-oiled machine. It commenced with monthly, three-hour seminars held from February through April. These sessions provided comprehensive instruction on essential trail skills, including basic first aid, effective tick management, tent setup, outdoor cooking techniques, water purification, and map reading. Complementing this practical training, a dedicated leadership class utilized case studies and reflective exercises to hone crucial skills such as communication, team motivation, and decision-making.

Physical training commenced a month prior to Labor Day. The regimen began with foundational exercises like push-ups, sit-ups, and extended jogs. It progressively incorporated 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—and with some members blindfolded. Competitive elements, including obstacle course relay races, were also introduced, 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. Groups practiced their navigation skills by locating a series of checkpoints, staffed by upper-level students, which ultimately guided them to their campsite. The subsequent week involved a thorough review of the preceding hike, identifying both successes and areas for improvement, along with supplemental training tailored to address identified problem areas. “After all of that, whatever anxiety I had about the trail had pretty much vanished,” remarked 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

Both Brooks and Cassidy attest to the profoundly life-altering impact of their St. Benedict’s backpacking expeditions. For Cassidy, witnessing his teammates surmount their self-imposed limitations and collaborate effectively to achieve a goal that many had initially deemed impossible left an indelible mark. He actively volunteered with the program as an upperclassman and continued his involvement while pursuing his college education. 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,” Cassidy, now 54, observed. He assumed the role of program director in 2007 and has since guided approximately 7,000 students through this experience. “The experience teaches kids important lessons about who they are, the world, their place in it, and the value of friendship,” Cassidy stated. Many of the students hail from urban environments and have never ventured far from the city, let alone experienced the profound tranquility of gazing at the stars from a mountaintop. Assisting young individuals in accessing such transformative experiences has become his vocational calling.

Brooks’s career path, while perhaps more circuitous, followed a similar trajectory. The AT trek ignited a lifelong passion for nature, wild spaces, and the remarkable sense of peace that envelops one during a walk through the forest. These hikes provided a crucial counterbalance to the 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 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 shared. His commitment led him to volunteer with organizations like Outdoor Afro, culminating in 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 remarked, his voice filled with contentment. “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 own hiking experience. Her background as a dedicated volleyball player and athlete had instilled in her a strong sense of confidence regarding the physical demands of the trek. She had envisioned herself as the steadfast supporter, carrying extra weight for exhausted classmates and offering them a literal and figurative shoulder to lean on. The unfortunate broken collarbone, however, dramatically altered these expectations. She was limited to carrying a minimal pack and found herself unable to perform basic tasks like tying her boots or setting up her tent. It was then that her friends stepped in to fill the void. “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.”

Consequently, Galo embraced the role of the team’s chief cheerleader. She would hike alongside friends whose spirits had begun to wane, reminding them of their progress and the personal growth they had achieved. She orchestrated 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 subsequently became a mentor for incoming first-year students and eagerly volunteered to assist with the current year’s hike. Her engagement with the outdoors further expanded as she 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 reflected. While her future academic and career plans remain in flux, one certainty has emerged: she is resolutely committed to dedicating ample time to nature, mountains, and the enriching pursuit of backpacking.