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


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


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.


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.


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

Spotlight: Amy Selinger — Overland Student, Leader & Parent

Teamwork & Leadership

Overland founder Tom Costley and Amy posing together in a vintage photo

When the Selingers invited Overland founder Tom Costley to give a slideshow back in 1984, they probably didn’t think their daughter, Amy, would sign up for one of the first ever Overland trips. Amy didn’t think that she would lead for three summers after college, pioneering the first trip through the Alps. And they definitely didn’t think Amy would find herself some 35 years later, dropping her own daughter off for her own teen adventure travel on the Alpine Challenge. But something has kept her coming back.

Amy’s first Overland trip was a bike trip through Maine and New Hampshire led by co-founders Tom and Liz Costley. A suburban girl, Amy said her parents waited every day to get the phone call that their daughter actually didn’t know how to bike. But the phone call didn’t come. In fact, that first trip gave Amy a taste of something she loved: a team that cared only about the team’s success — not the individual’s.

The last night of Amy’s first Overland trip, she remembers feeling something that will be familiar to all Overland students. Sitting around the fire and studying the faces of her trip mates, she couldn’t believe how little she knew them at trip start; she couldn’t believe how well she knew them now.

This need to be a part of something bigger than herself kept Amy coming back over the years. After college, she led Cape Cod & the Islands one summer, then Pacific Coast, and then the first iteration of the Alpine Challenge. Amy thinks back on biking across the Golden Gate Bridge with her group of students as one of the most triumphant experiences of her life. As a future educator, the fact that she could provide young people with this experience was so empowering.

Hannah on the Alpine Challenge participating in teen adventure travel
Hannah with her Alpine Challenge leaders Jake & Lucinda
Hannah posing with her group on Alpine Challenge while taking a break from hiking
Hannah’s Alpine Challenge group

When asked what prompted her to send her own kids on Overland trips, Amy talked about how there can be such a focus on the individual growing up in today’s phone-infested era. There’s the pressure of grades, of social media, of increasingly competitive high schools.

Julia and friends pose in Yellowstone during their teen adventure travel trip
Julia on Yellowstone Teton Explorer
Julia whitewater kayaking in Yellowstone and the Tetons
Julia on the Snake River

In contrast, Overland has maintained this focus on the success of the group even though the organization itself looks so different. The trips are more ambitious and better equipped. Amy would know — she’s the one hosting slideshows now in the home she shares with her husband (and former Overland co-leader), Mark. But the important things really haven’t changed. You only make it up the mountain if everyone makes it up the mountain.

That sense of group accomplishment allowed Amy to look at herself in a whole new light. “You can’t give someone self-esteem,” Amy said. “It has to be earned.” And Amy? She wanted to give her kids the chance to earn it.

Amy's family pose together and smile outside
Amy, Hannah, Mark & Julia

Editor’s Note: Just as Amy biked across the Golden Gate Bridge on her own Overland trip, and Hannah climbed through the Swiss Alps, and Julia learned how to whitewater kayak, every Overland student finds his or her own challenge to accomplish. On our trips, students are able to push their own boundaries while relying upon the support of a wholesome, nice group to make the journey all the more fun. Read more about the experience Hannah would have had on her Alpine Challenge teen adventure travel trip here.

Filed Under: Teen Summer Adventures / Teen Adventure Programs / Student Experiences

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