The Joy is in the Challenge

Independence & Self-Reliance

the joy is in the challenge featured

Sleeping in a tent for the first time. Summiting Mount Kilimanjaro, the highest peak in Africa. Ordering food at a traditional French market. Learning to cook over a camp stove. Painting a mural at a school in Costa Rica. Riding your bike from Georgia to Southern California.

Berkshire Adventure tent group

With so many different trips to discover, every Overland experience is unique. The mix of students, the carefully-selected leaders, and the trip itinerary vary to build something special and distinct. But the true constant of every Overland trip is challenge: asking more of the group and allowing them to show what they can achieve with hard work and their peers’ support.

For some trips, the challenge is physical: American Challenge (bike across the United States); Alpine Challenge (hike the Alps and summit the Mettelhorn); Field Studies Peru (trek to Machu Picchu).

Smiles at the summit of Mount Kilimanjaro

For other trips, the challenge lingers below the surface: Writing & Hiking New England (sharing a piece you’ve written with the group for feedback); Yellowstone Teton Adventure (whitewater rafting on the Snake River); Language & Service Costa Rica (collaborating with students and teachers in a language you’re still working to master).

But on every trip, beyond the highlights of the itinerary, there are unexpected challenges that will make a lasting impression. The challenge of waiting until everyone in the group has been served to say “cheers” and dig in to dinner. The challenge of being away from home — maybe for the first time. The challenge of getting along with group members who may have very different backgrounds and experiences than your own.

Hiking above Tahoe on Sierra Adventure
Northwest Expedition backcountry hike in Olympic National Park

Every Overland student — from 10-year-olds on an introductory trip to 18-year-olds about to start college — leaves their trip with the confidence that comes from conquering an experience they didn’t think they could. Every student ends the summer knowing they can push themselves, take risks, and lean on the group — and that no great accomplishment comes without challenge. These are the lessons that last well beyond an Overland teen summer adventure camp, and they’re the common thread across our 46 trip offerings and countless group adventures. Whether you’re sleeping in a tent for the first time or summiting Kilimanjaro, the joy is in the challenge.

Berkshire Adventure at Mt. Greylock summit

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