Why Families Come Back to Wilderness Adventures Year After Year

This summer, I had two conversations that have stayed with me.

Both were with mothers who had participated in Wilderness Adventures trips back in the 1990s. Both had sent their sons on Wilderness Adventures trips this summer.

And both shared something remarkably similar about why they made that decision.

They remembered.

They remembered the extraordinary places they had explored. The friendships. The discomfort. The independence. The feeling of being somewhere completely new, surrounded by people who started as strangers and became something much more.

More than 30 years later, those experiences still mattered enough that they wanted their own children to have them.

I’ve been thinking about that a lot.

As parents, we spend an extraordinary amount of time deciding which experiences are worth giving our children. We consider the cost, the logistics, the opportunities, and whether our children are ready.

But what if we asked a different question: What experiences will still matter to our children 30 years from now?

One Summer Often Leads to Another

At Wilderness Adventures, we see something special happen when students return for a second, third, or fourth summer. 

In 2026, nearly one in three Wilderness Adventures students was returning for another adventure. Some were back for their second summer, others for their third or fourth, and some had been traveling with us for five summers or more.

What keeps them coming back?

Sometimes it’s the destination. A student who explored Yellowstone one summer might be ready to backpack in Alaska the next. Another who discovered a love of hiking might want to try sea kayaking, rock climbing, or international travel.

But I suspect the real reasons go much deeper.

Students come back because they remember how they felt.

They remember the satisfaction of doing something hard. The friendships formed while cooking dinner together, laughing in the back of a van, or sitting around camp after a long day. They remember the Trip Leader who believed in them, the moment they realized they could do something they hadn’t thought possible, or the extraordinary feeling of being part of a community. (Read more about the power of the journey here).

And they want to experience it again.

The Adventure Grows With Them

One of the things I love most about Wilderness Adventures is that the experience doesn’t have to end after one summer.

A younger student might begin with a shorter trip closer to home, learning to pack a backpack, set up a tent, and navigate life away from family.

The next summer, they’re ready for something more.

A longer backpacking trip. A new destination. A different outdoor skill. Greater responsibility within their group.

And by their third or fourth summer, that same student may be ready for an ambitious adventure that would have seemed unimaginable a few years earlier.

The destinations change, but so does the young person.

The student who once needed help organizing their gear becomes the one helping somebody else.

The student who was nervous about making friends becomes the one welcoming a newcomer.

The student who struggled through their first challenging hike becomes the one encouraging a teammate up the trail.

Each summer builds on the last, not simply through bigger adventures, but through growing confidence, independence, and leadership.

That’s the beauty of returning. Students aren’t repeating the same experience. They’re discovering what they’re capable of next.

The Friendships and Lessons That Last

Recently, we put out a call on LinkedIn to reconnect with former Wilderness Ventures (yes, Wilderness Ventures is now Wilderness Adventures!) and Wilderness Adventures students, Trip Leaders, and staff.

We asked a simple question: What year were you here, and where did WA take you?

The responses were wonderful.

Alumni started sharing stories, old photographs, destinations, and memories from summers spanning several decades.

One former student, Maggie Cowling, remembered four consecutive summers: Hawaii in 2004, Ecuador and the Galápagos in 2005, Alaska in 2006, and another Alaska adventure in 2007.

But what stood out wasn’t just the list of destinations.

Maggie shared that a Trip Leader from her 2006 adventure helped her secure an internship at Grand Teton National Park, an opportunity that eventually led to her career.

Another alumnus, Shannon Bond, recalled five Wilderness Ventures trips during the late 1980s and early 1990s. His adventures progressed from backpacking and rafting in the Rockies to cycling, kayaking, the North Cascades, and eventually an Alaska leadership course.

Five different trips. Five different opportunities to grow.

And decades later, the memories were still there.

These are the stories that remind me why this work matters.

A summer adventure might last two, three, or five weeks. But the relationships, interests, confidence, and possibilities that emerge from it can last far longer.

The Legacy Becomes a Family Story

One of my favorite examples comes from an old friend, Alston.

Alston participated in Wilderness Ventures trips in the 1990s, returned as a Trip Leader in the early 2000s, and eventually worked full-time for the organization.

She also met her husband through Wilderness Ventures. He, too, had been a participant and Trip Leader.

Now, more than two decades later, they’re preparing to send their own child on a Wilderness Adventures trip to Alaska.

In a recent alumni conversation, Alston described her time with Wilderness Ventures as the best experience of her life. I wrote about reconnecting with Alston and her husband in an earlier newsletter. 

At the time, we were reflecting on how much the program had evolved—and how much of its essential magic remained the same.

The wild places. The friendships. The laughter. The discomfort. The responsibility of being part of a group. The remarkable independence that comes from being away from home and fully immersed in an experience.

In the 1990s, being disconnected wasn’t a special feature of a wilderness trip. There simply weren’t smartphones to check, photographs arriving on parents’ phones, or constant updates from the trail.

Young people went away, had experiences that belonged to them, and eventually came home with stories to tell.

Today, we have to be much more intentional about creating that space.

But the opportunity is just as powerful.

And when former students become parents themselves, they understand something that can be difficult to appreciate until years later. The greatest gift wasn’t necessarily the destination, it was who they became along the way.

More Than a Summer

I love that Wilderness Adventures has been introducing young people to extraordinary places since 1973. But what I love even more is the idea that our work doesn’t end when a student comes home.

Sometimes they return the next summer, ready for a new adventure.

Sometimes they return three years later, having discovered that the outdoors has become an important part of who they are.

Sometimes they return as Trip Leaders, eager to create the same experiences for another generation.

And sometimes, 30 years later, they call us because they have a child of their own who is ready to go.

Of course, we hope students come back for a second, third, or fourth summer. We love watching them grow, challenge themselves, build friendships, and discover new corners of the world.

But ultimately, we hope Wilderness Adventures becomes something much bigger than a summer trip.

A launchpad. A place where young people discover what they’re capable of—and carry that knowledge into whatever comes next.

And if we’re lucky, someday they’ll want to share that gift with someone they love.

 

By, Anne Izard