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Thirty-three trips into the wilderness. 68 student leaders. 287 student participants. Plus dozens of canoes, tents, sleeping bags, rain gear, pounds of cheese, and other essentials. The planning that goes into Hamilton’s Adirondack Adventure (AA) orientation program is extensive, and the process has run like a proverbial well-oiled machine for the past four decades thanks in large part to Director of Outdoor Leadership Andrew Jillings, who came on board in 1997 to expand the program from a modest six trips.

But what happens to that “machine” when its coordinator suffers a fall and breaks several bones just 10 days before trips are about to begin?

Andrew Jillings at Reunions '24
Director of Outdoor Leadership Andrew Jillings at Reunions ’24. Photo: Nancy L. Ford

The Hamilton community steps up, of course. Associate Director of Outdoor Leadership Sarah Skoy describes what Jillings brings to orientation as Big Andrew Energy. “He can make magic happen,” she told the student leaders. “We’re going to have to level up — all of us — to make orientation great for our new students.”

They did just that. By all of us, Skoy called in several alumni, who have been integral to the program, to assist with training student leaders and coordinating trip logistics. They flew in on short notice from full-time lives in Texas, Washington, D.C., Philadelphia, Maine, and Colorado. This year these alumni took on key responsibilities as Jillings recovered from his injuries. (He’s progressing nicely, by the way!)

We’re going to have to level up — all of us — to make orientation great for our new students.

Sarah Skoy Associate Director of Outdoor Leadership Sarah Skoy

It Takes a Village

Zach Weller ’23, who describes his involvement with outdoor leadership at Hamilton as a second major, parlayed his experiences with Hamilton’s Outdoor Leadership program into a job after graduation with Backroads Travel, where he spent two years leading hiking trips in Scotland and Ireland. He recently moved to Colorado where he’s begun graduate studies in counseling psychology at the University of Denver.

Adventure Trips at Hamilton

All Hamilton incoming first-year and transfer students participate in an Orientation Adventure trip. This year’s program included:

  • 33 excursions for Adirondack Adventure (AA)
  • 23 Outreach Adventure (OA) and Exploration Adventure (XA) trips
  • 6 Outdoor Adventure Sampler trips designed to introduce students to a variety of outdoor-related activities. 

“Whether it was paddling a boat in the Adirondack 90 miler, organizing 46 peaks as an Outing Club officer, or leading first-year students on AA trips, the impact of Hamilton Outdoor Leadership on my time at Hamilton was profound,” he said.

Weller credits the relationships he formed with mentors Jillings and Skoy with not only launching his career path, but that of several other former students who are now in outdoor leadership director roles at liberal arts colleges across the country. “That’s a testament to how strong our program is,” he added.

This year in Jillings’ absence, Weller worked closely with Skoy to train AA student leaders, who arrive on campus several days before new students. He also helped plan and run logistics, which ranges from organizing transportation for participants, kayaks, and canoes to coordinating any potential evacuations. The ultimate goal is to create an experience that helps incoming students transition into college life by fostering connections with peers and developing a sense of community through spending time in the outdoors.

“I hope that everyone who comes in contact with outdoor leadership at Hamilton has a meaningful experience. Whether that is on an orientation trip their first few days of college or farther down the line through any number of activities that are put on by outdoor leadership, I truly believe that anything you put into the program you will get back tenfold.”

Quinn Brown ’24 agrees. A native of rural Maine, he came to Hamilton no stranger to spending time in the outdoors. He served as an AA trip leader through the summer after graduation before embarking on a year of traveling (and camping) across the country. He just started as an apprentice sixth-grade teacher at the New Canaan (Conn.) Country School, where he’ll no doubt apply some of the lessons learned through Adirondack Adventure.

“The time spent off campus in small groups is so helpful to helping first-year students develop a sense of belonging when they get back to campus,” Brown said. “Even if participants often move on to different friendships and activities beyond their trip theme, the friendships students make on their trips provide them with connections all across the different parts of campus that I think helps build a cohesive, inclusive campus environment.”

Brown was joined by Maggie McDow ’23, who works at the Nature Forward Preschool outside Washington, D.C. The two alumni came back to College Hill to help AA student leaders with both technical skills — such as setting up tents and tarps, stove mechanics and repair, map and compass orienteering — and interpersonal activities like field initiatives and social facilitation training. They were also involved with facilitating disaster scenario practice.

“It’s a testament to Hamilton’s Outdoor Leadership program that there are multiple alumni who have not only gone on to work in outdoor education, but who saw such value in the program that we were willing to drop everything to come back,” said McDow, who got the call from Skoy on a Friday and by Tuesday was on her way to campus. 

Like McDow, Brown sees his ongoing involvement in AA as paying forward an experience that meant so much to him. “There are few things that bond people together more than sharing a tent on a cold, rainy night,” he said. “Outdoor leadership programming serves as one model for community and collaboration that can be transposed onto our lives within modern society. These experiences may not teach you how to solve a math problem or write an essay, but they will help you hone personal qualities and interpersonal skills that are essential to success in just about every part of your life.”

[Outdoor leadership] experiences may not teach you how to solve a math problem or write an essay, but they will help you hone personal qualities and interpersonal skills that are essential to success in just about every part of your life.

Quinn Brown ’24 Quinn Brown ’24

Reporting for ‘Trink’ Duty

Sarah Hossain ’18 and Jennie “Jx” Wilber ’17 have each earned their “Golden Trowel” — a coveted award Jillings presents to alumni who’ve returned for 10 years to help with orientation.

For Wilber, who has led trips for AA as well as OA and XA, this was her 12th year of service. (She had intended to “retire” after last year, but decided to come back after Jillings’ accident.) Hossain just completed her 11th year with AA. She describes returning each fall like coming home to the community that shaped who she is.

“I make time for it, even if I have to travel or take time off work, because this program has had such a lasting impact on me personally and professionally,” said Hossain, a dermatology technician in Dallas who is applying to Physician Assistant programs. “Leading AA trips has taught me the value of connecting with others, embracing uncertainty, trying new experiences, and ‘being here now,’ which means to be mindful of the present moment and feeling it fully without distraction. These skills have been useful in my everyday life and as a young adult starting a career.

“Jx actually said it best — coming back for AA each fall feels like putting on my favorite old t-shirt,” Hossain added.

An example of
A leader on "Trink" support duty from Adirondack Adventure 2019. Photo: Nancy L. Ford

While on campus for three-four days each fall, Hossain and Wilber provide “Trink” support. The Trink (turf field + ice rink) is where each trip gathers prior to their departure to take inventory of their gear, food, and supplies. Much of the day is spent fielding questions about itineraries, food allergies, or gear organization. In the evening, last-minute necessities are picked up during a shopping run and delivered to the Trink for leaders to pick up.

“What brings me back each year is part the program and part the people,” Wilber said. “I believe in what the orientation programs are doing. I’ve seen how experiential education affects students far beyond the first week of freshman year, and it’s a thrill to be part of such a large, meaningful operation. The other part is the people: fellow leaders, incoming freshmen, and the leadership team have all become good, lifelong friends, and a lot of that started on the football field on move-in day.”

Long-Lasting Lessons

Wilber, who works as a financial planner outside Philadelphia, often thinks back to her first experience with AA when she was a first-year student back in 2013. It was the first time she participated in the tradition of “letter to self,” an exercise where orientation leaders guide trip participants in writing a letter to be mailed to them in the future.

“Sometimes it’s around a campfire, spread out along the shore of a lake, or anywhere else that gives you a chance for quiet reflection and to write, confidentially, whatever you want to your future self,” Wilber recalled.

The letters are then sealed and addressed with the author’s name, mailbox number, and a semester/year for when they are to be delivered. “While most students write one while on their participant trip, I’ve been able to write myself 12 times throughout the years of leading trips and supporting the program,” she said.

Other AA participants-turned-alumni-volunteers have found similar opportunities for self-discovery. Brown said the outdoors provides the perfect atmosphere for learning to “Know Thyself” (Hamilton’s motto) and for community-building.

“When AA celebrated its 40th anniversary last year, I realized I’ve been involved for over a quarter of its history,” Hossain said. “That perspective is one reason I knew I had to step in again this year after Andrew’s injury. I was in good company, too. Several alumni dropped everything to return and support the program. To me, that speaks volumes about AA’s impact. The friendships and community it fosters are strong enough to last long after our time as students comes to an end.”

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