St. Benedict’s Preparatory School’s 50-Year Appalachian Trail Tradition: A Rite of Passage Forging Resilience, Teamwork, and Lifelong Bonds

Published August 7, 2026, 01:05 PM

The uncharacteristic May heat mirrored the internal inferno raging within 15-year-old Lilliana Galo: fatigue, frustration, and a desperate longing for the hike to end. It was 2025, and Galo, along with seven classmates, was three nights into a demanding five-day trek along a 55-mile stretch of the Appalachian Trail through New Jersey. Nine miles had already been conquered that day, with one or two more to go before they could establish camp. Every fiber of her being ached, from the raw soles of her feet to the throbbing collarbone she had fractured just days before the expedition began. Yet, a flicker of resolve ignited within her. “Discipline,” she whispered to herself, her gaze snapping to her feet, focusing on the simple act of placing one in front of the other, avoiding any hint of a drag. Drawing a deep breath, she ascended another of the numerous small knobs that characterized the Kittatinny Mountain ridge. The arduous climb eventually yielded to a brief, welcome descent, met with a collective cheer from her group. Hiking at the rear, Galo looked up to see her companions, clad in a motley assortment of hand-me-down boots and packs that evoked images of a bargain-bin sale from a decade prior. They were linked arm-in-arm, their laughter echoing through the trees as they carefully navigated the downhill slope.

“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.” In that moment, the lessons imparted by teachers, upperclassmen, and alumni throughout the year coalesced into a profound understanding for Galo. She found herself showering her friends with praise and encouragement, a surge of pride washing over her. “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 arduous 55-mile trek represents the culmination of a mandatory rite of passage for all first-year students at St. Benedict’s Preparatory School, a private institution in Newark, New Jersey. For over half a century, rising sophomores at this esteemed academy have embarked on this self-guided leadership and team-building exercise on the Appalachian Trail in late spring. The program, deeply ingrained in the school’s ethos, aims to foster essential life skills in young men and, since its merger with a neighboring school in 2017, young women.

Each incoming class, typically comprising around 190 students, is divided into smaller groups. These cohorts then undertake the hike and camping in staggered intervals along the trail. Within these teams, students are assigned distinct roles—such as navigator, cook, medic, or captain—necessitating a profound reliance on each other for success. The absence of phones and electronic devices is a deliberate choice, forcing students to engage fully with their environment and each other. While two faculty members, administrators, or upper-division students accompany each group as chaperones to provide assistance in emergencies, their role is strictly supervisory, offering no direct help with decision-making or logistical support beyond moral encouragement. Significantly, the vast majority of these students enter the program with minimal, if any, prior backpacking experience. Many have had limited exposure to the wilderness, let alone the challenges of backcountry travel.

Glenn Cassidy, the current program director and a proud alumnus of St. Benedict’s, graduating in 1990, elucidates the program’s core objectives. He explains that the experience is meticulously designed to propel students beyond their urban comfort zones, immerse them in the enduring benefits of nature, and present them with an immersive challenge that cannot be overcome in isolation. The ultimate goal is to cultivate resilience, bolster self-confidence, and instill a profound appreciation for the power of a cohesive team working in unison. Beyond these tangible outcomes, the Appalachian Trail hike serves as a formal and deeply meaningful 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 states, her voice resonating with the significance of the tradition. “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.”

A Legacy Forged Over 50 Years on the Appalachian Trail

The unique, full-class program at St. Benedict’s is, according to Cassidy, unparalleled in the nation. Its genesis in 1973, however, was almost serendipitous, a testament to innovative leadership and a profound belief in the transformative power of experiential learning. The institution that predated St. Benedict’s Preparatory School was founded in 1868, serving a predominantly working-class community comprised of German, Irish, and Italian Catholic immigrants for approximately a century. However, the turbulent decades following the Newark race riots of 1967, coupled with significant white flight, led to the closure of the predominantly Caucasian school in 1972. A small but determined group of monks subsequently reformed and reopened a significantly scaled-down version of the school just a year later.

The core mission of educating underserved populations remained, but the socio-economic landscape had dramatically shifted. Newark had become one of the nation’s most impoverished urban centers, with nearly 60 percent of its residents living in federally designated low-income areas by 1980. The relaunched school attracted a student body that was overwhelmingly Black and brown. In response, the new administration implemented robust scholarship programs and generous financial aid packages to ensure that tuition remained accessible to families from all economic backgrounds.

Cassidy emphasizes that the founders recognized the critical importance of deep educational engagement in breaking the systemic cycle of poverty. Experiential learning was thus elevated to a central tenet of the curriculum. Administrators initiated an annual spring project where students were divided into small groups and immersed themselves in subjects aligned with their professional interests. These project teams spanned a diverse range of disciplines, including architecture, photography, art, and medicine, among others.

It was in 1973 that the founding headmaster, Edwin Leahy, conceived of a groundbreaking idea: to take students on a multi-day hike along the Appalachian Trail. He envisioned this challenging journey as a powerful means to introduce them to the profound quietude and self-regulatory benefits of nature. A rigorous backpacking adventure of over 50 miles, he believed, would effectively instill invaluable values such as discipline, teamwork, and unwavering perseverance. Moreover, the extended time in the wilderness would provide a unique opportunity for meaningful conversations, ranging from effective strategies for managing difficult emotions to discussions about home life, 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 practical challenges, Leahy remained steadfast in his conviction that the trek held the potential to fundamentally alter the life trajectories of these young men. The school’s decision to become coeducational in 2017, through a merger with a neighboring institution, further broadened the impact of this transformative program.

Leahy’s commitment to the expedition was unwavering. He meticulously acquired maps and consulted relevant literature, and then devised a rigorous training regimen. Students engaged in intensive physical conditioning, including exercises such as walking the school grounds while carrying 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, clad in their everyday sneakers and equipped with school backpacks filled with snacks and jugs of water, embarked on a 20-mile road walk. “They were so inexperienced that it took forever,” Cassidy remembers. “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 itself was not without its share of mishaps and humorous misadventures. One student, demonstrating a remarkable lack of preparedness, arrived with his mother’s rolling luggage. Another had ingeniously, albeit impractically, secured a set of cast-iron pans to his shoulder straps. Appropriate footwear was virtually nonexistent; diets largely consisted of peanut butter and jelly sandwiches; and tents were sourced from general merchandise stores. With no dedicated support team and the absence of mobile phones, the hike was an unequivocal make-or-break experience. At one point, a student, overwhelmed by the exertion, sat down resolutely in the middle of the trail, refusing to proceed. Leahy, employing a bold tactic, informed him that they would simply see him the following year, implying his survival of the intervening twelve months was not guaranteed. Fortunately, this stark pronouncement 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 these initial challenges, the program undeniably demonstrated its profound potential. The shared hardships of the quest forged an unbreakable bond between the boys and their headmaster, and among themselves. They returned to the school not merely as participants but as conquering heroes. The mutual respect and camaraderie cultivated on the trail proved instrumental in their integration into the St. Benedict’s community, and remarkably, behavioral problems among the students promptly diminished.

The Program’s Evolution: From Humble Beginnings to Institutionalized Excellence

The resounding success of the initial expedition inspired Father Leahy to formally institutionalize the annual trip. This mission received a significant boost two years later when a new teacher, Mark Payne, an avid outdoorsman and seasoned Scoutmaster, volunteered to assume leadership of the nascent program. Payne, himself an accomplished backpacker, firmly believed that the pioneering Appalachian Trail trek held immense transformative potential for both the students and the school as a whole. However, he recognized that unlocking this potential required a more structured and comprehensive approach.

This critical overhaul of the program drew upon a rich tapestry of influences, including established Boy Scout protocols, fundamental conservation principles, and the core school values, eloquently encapsulated in mottos such as, “Whatever hurts my brother, hurts me.” Payne expanded the scope of the experience to encompass all first-year students and seamlessly integrated it into a broader, year-long agenda meticulously designed to foster a strong sense of school identity and belonging.

“When you sign up to go to Benedict’s, you know about the hike,” says Galo, whose older siblings had attended the school and whose tales of their backpacking adventures had achieved legendary status within their family. “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 in essential trail skills, including basic first aid, effective methods for handling ticks, proper tent setup, outdoor cooking techniques, water management, and the art of reading topographical maps. Complementing this practical instruction, a dedicated leadership class utilized case studies and reflective exercises to hone critical skills such as effective communication, team motivation, and sound decision-making.

Physical training commenced a month before Labor Day, the traditional start of the academic year. The regimen began with foundational activities like push-ups, sit-ups, and sustained jogs. It gradually progressed to more challenging exercises, such as the complex maneuver of walking a pair of oversized skis across a field, with half the team facing forward and the other half backward—and some members blindfolded. The training also incorporated competitive elements like obstacle course relay races, where platoons were tasked with strategically positioning teammates based on their individual strengths and weaknesses.

The next crucial phase involved an overnight trial hike in Stokes State Forest. Here, groups practiced their navigation skills by locating a series of checkpoints manned by upper-level students, which ultimately guided them to their designated campsite. The following week, a thorough review session was held, analyzing both the successes and shortcomings of the practice hike. This debriefing often included supplemental training tailored 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 Careers

Both Brooks and Cassidy unequivocally attest to the profoundly life-altering impact of the St. Benedict’s backpacking trip. For Cassidy, witnessing his teammates conquer their self-doubt and collaborate to achieve a goal that many had initially deemed impossible left an indelible mark on him. He actively volunteered with the program as an upperclassman and continued to offer his support while in college. These formative trekking experiences ultimately inspired him to accept a position as an athletics director and assistant to Mark Payne in 1994.

“There’s something magical that happens out there,” remarks Cassidy, now 54, who assumed the role of program director in 2007 and has since guided approximately 7,000 students through the program. “The experience teaches kids important lessons about who they are, the world, their place in it, and the value of friendship.” He highlights that many students come from urban environments, having never ventured far from the city, let alone gazed at the stars from a mountain summit. The opportunity to facilitate these transformative experiences for young people became a deeply fulfilling calling.

Brooks’s career trajectory, while perhaps more circuitous, followed a similarly inspired path. The AT trek instilled in him a lifelong passion for nature, wild spaces, and the remarkable tranquility that envelops one during a forest walk. These hikes provided a vital counterbalance to the stresses of demanding jobs with major New York City television networks and media companies. As the year 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 states. His engagement with organizations such as Outdoor Afro led to his obtaining training certifications and ultimately secured him 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 with evident satisfaction. “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 Appalachian Trail experience. Her background as a dedicated volleyball player and athlete had initially fostered a strong sense of confidence in her physical capabilities. She had envisioned herself as the one providing support, carrying extra weight for exhausted classmates, and allowing them to lean on her strength. However, the broken collarbone shattered these preconceptions. She was relegated to carrying a minimal pack and found herself unable to perform basic tasks like tying her boots or setting up her tent. It was her friends who 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.” In this new capacity, Galo embraced the role of the team’s chief cheerleader. She walked alongside friends whose spirits had begun to wane, reminding them of their remarkable growth and resilience. She initiated pep talks during breaks and encouraged the group to pause and appreciate the simple beauty of a gurgling creek or a breathtaking 2,000-foot vista.

Galo’s experience on the trail 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. Furthermore, she participated in a summer outdoor learning program at Grand Teton National Park, further deepening her connection with the natural world.

“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 fulfillment of backpacking. The enduring legacy of St. Benedict’s Appalachian Trail tradition continues to shape lives, instilling in its students a powerful combination of self-reliance, mutual support, and a lifelong appreciation for the transformative power of the wilderness.