We Welcome Your Application to Join Us!

We build each of our groups with care, keeping the groups small (no more than twelve students), and paying close attention to age, grade, gender, and the mix of hometowns and schools. Our goal is to put together great groups — groups where nice kids thrive in a supportive, wholesome, and caring environment. Please note: availability as shown is based on students traveling without a friend; if your child is interested in traveling with a friend, please call our office for availability.

Important Information about Availability

Available

This departure of this trip has good availability. Apply as soon as possible since availability changes quickly.

Limited

This departure of this trip has limited availability. Apply as soon as possible, and on receipt of your application, if space is still available, we’ll confirm a spot for you. If all of the spots are taken, we’ll call you to discuss options.

Call

This departure of this trip is currently full — please call us to discuss options.

How to Apply

Apply online using a credit card for the $795 deposit (your card will not be charged until we confirm a spot for you). Applications are reviewed in the order in which they are received (we do not hold spots over the phone).

When to Apply

The flow of applications starts in July and peaks in January/February. Some groups fill by the December holidays, and others will have space into the late spring. Our advice? Apply as soon as possible — it only takes a few minutes — and we’ll get to work right away to find a great spot for you.

Questions?

Call (413.458.9672) or email (info@overlandsummers.com). We look forward to hearing from you.

The Joy is in the Challenge

Independence & Self-Reliance

Teens pose after biking across the country on a teen summer biking trip

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.

Three girls in a tent smiling on their summer hiking trip in the Berkshire Mountains.
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).

A group at the summit of Kilimanjaro smiling after a challenging hike during their trip to Tanzania.
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.

A boy hiking in a baseball camp smiles with Tahoe and pine trees in the background.
Hiking above Tahoe on Sierra Adventure
A group smiles together wearing backpacking packs in a forest of the Pacific Northwest.
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.

A group and their leaders holding an Overland sign at the summit of Mount Greylock during a summer hiking trip.
Berkshire Adventure at Mt. Greylock summit

Filed Under: Teen Summer Adventures / Teen Adventure Camps / Summer Hiking Trips


Similar Blog Posts

Three girls carrying their sleeping bags as their summer trip begins.

Trip Start – Build-Up, Preparation, Nervousness, Excitement

Teamwork & Leadership

As any Overland student knows, preparing for your trip can be a bit nerve wracking. Whether you’re embarking on Berkshire...

Teens pose after biking across the country on a teen summer biking trip

The Joy is in the Challenge

Independence & Self-Reliance

Sleeping in a tent for the first time. Summiting Mount Kilimanjaro, the highest peak in Africa. Ordering food at a...

A girl smiles while riding her bike and wearing a helmet in front of a hill covered in pine trees.

There’s Beauty Out There

Discovery & Inspiration

It can be easy to forget how much beauty there is out there. Social media, breaking news, name-calling, and an...

All Blog Posts