When Dan Shapiro ’68 thinks back on Midland, the first image that come to mind are not singular moments, but a feeling of place.

“I picture Upper Yard, looking out toward Grass Mountain,” he recalls. “Watching deer move across the hills during class. Huddling around a wood stove trying to keep warm. Being outside as much as was possible.”

For Dan and his classmates, Midland in the mid-1960s was not an easy place – and that was precisely the point. Students carried real responsibility, learned through challenge, and spent countless hours moving through the land that surrounded them. Dan served as cross-country team captain, running daily over uneven trails, leaping fallen trees, dodging gopher holes, and learning – quite literally – how to keep his footing.

“We didn’t call it trail running back then,” he said with a laugh. “But that’s exactly what it was. You learned to be aware, to adapt, to keep going.”

A Class Bound by Experience

The Class of 1968 was small, diverse, and unusually tight-knit. Many students arrived not knowing one another, but years of shared work, shared hardship, and shared time outdoors forged lifelong bonds. Even decades later, Dan and his classmates still gather regularly to camp and hike together – from Joshua Tree to the Eastern Sierra.

“It wasn’t something we planned.” Dan said. “We just kept showing up for each other.”

That enduring connection – to one another and to the outdoors – would later inspire the creation of the Wilderness Fund, a way for the class to give future Midlanders access to similarly formative experiences.

Grass Mountain Day: Then and Now

Long before the Wilderness Fund existed, the Class of ’68 helped shape one of Midland’s most beloved traditions: Grass Mountain Day. What began as a student proposal for a backcountry hiking day has become a rite of passage – anticipated, respected, and remembered by generations of students.

Seeing it endure has been especially meaningful for Dan.

“Grass Mountain is symbolic of Midland,” he said simply.

He still remembers his first solo ascent as a freshman – reaching the summit just as fog rolled in and daylight disappeared. With no flashlight and little experience, he found his way down in the dark, navigating steep ravines and fields of yucca.

“I probably shouldn’t have done it alone,” he admitted. “But I learned something that day.”

That lesson – awareness, humility, perseverance – is one Dan sees echoed each year as students prepare for and take on Grass Mountain Day themselves.

Why Wilderness Still Matters

For Dan, the power of wilderness education lies not just in the physical challenge, but in what it cultivates internally.

“Midland taught me self-reliance,” he said. “Confidence. Situational awareness. You learn what you’re capable of, and that stays with you.”

That belief is at the heart of the Wilderness Fund: not simply funding trips, but creating moments that shift a student’s sense of self. Seeing students like Amelie Grant ’27 step into leadership – and return ready to mentor others – has been deeply affirming.

It’s a pivotal point,” Dan said. “You get students out of their heads. They realize they can do hard things. That confidence carries forward.”

A Legacy Still in Motion

Dan is quick to point out that when the Class of ’68 imagined giving back, they weren’t thinking in terms of legacy. They were thinking about opportunity – about helping students take a leap they might not otherwise afford.

“That’s the message,” he said. “Take the leap. Experience something that changes you.”

More than 50 years after graduating, Dan still hikes mountains where Wilderness Fund recipients have and continue to train. When he learned that Amelie’s course took place in the San Juan Mountains – terrain he himself has traveled – the connection felt almost surreal.

I know that place,” he said. “I’ve been snowed in there. Thunderstorms, high winds – all of it. Hearing her talk about it, I knew exactly what she meant.”

Looking Ahead

When asked what he hopes future students understand about the Class of ’68, Dan doesn’t hesitate:

“We were just kids,” he said. “But Midland gave us the tools to choose our own paths – and the confidence to walk them.”

It’s a philosophy still alive in the hills, on the trails, and in the traditions Midlanders carry forward – one step, one climb, one leap at a time.

Written by Jasmine Fullman, Admissions and Advancement Associate