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.

Dessert Circle

Teamwork & Leadership

A group sharing dessert in the Tetons during their summer hiking trip.

Every evening, on every Overland trip, students and leaders sit down (with a sweet treat, of course) to recap the day and listen to every member of the group reflect on their successes and challenges. At Dessert Circle, a longtime Overland tradition, students and leaders share three things over dessert: high, low, cheers.

As each day is an opportunity to create new memories, we’re always spoiled for choice of a “high of the day.” In my eight years with Overland teen adventure trips, my highs have included conquering difficult climbs, laughs on the trail, and celebratory moments like surprise ice cream cones or sprinkler runs.

A group sits together in the Serengeti of Tanzania during their service and hiking trip.
Field Studies Tanzania Dessert Circle

We share lows, too — not to dwell on difficult moments, but to recognize the ways we can be even more successful tomorrow and to acknowledge that working together and holding high expectations can lift us out of our lows. Every day has its frustrations, but we don’t let our lows define our Overland experiences.

And, finally, “cheers.” Cheers has always been my favorite part of Dessert Circle; it’s an acknowledgement and thank you to someone else in the group who did a little (or big!) something to brighten your day and support you. When we cheers a peer or leader, we’re showing someone that their contributions to the group don’t go unrecognized. We’re also shifting the focus away from ourselves: at Overland, the group always comes first.

As a leader, Dessert Circle has taken on even more significance for me. My highs are moments that I’ve been especially proud to see my students step up, rise to challenges and put the group before themselves. My lows are teachable moments from the day. My cheers are part of my commitment to meaningfully engage with every student every day.

A group of teens during sunset overlooking the Pacific Ocean during their summer hiking trip.
Northwest Expedition Dessert Circle

Dessert Circle is so important to the leader community that we take it beyond our time on trips. Daily at leader training, among Williamstown staff and even after the summer — in group chats and on social media — leaders share our highs, lows and cheers.

When we take time to reflect on our day and intentionally listen to our peers’ takeaways, too, we share valuable memories of today while also strengthening group community and looking optimistically to tomorrow.

From me to you, cheers.

A group eats together next to a lake in the Canadian Rockies after biking to their campsite.
Canadian Rockies & Montana Dessert Circle

Filed Under: Teen Summer Adventures / Teen Adventure Programs / Overland Traditions

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