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 (Continued)

Discovery & Inspiration

Campers stop for lunch during a teen adventure program this summer

Last week, our Founder and Director Tom Costley shared his reflections on the Overland tradition of Dessert Circle. Overwhelmed by the outpouring of memories and reflections from students and leaders, we’ve collected a few of the responses that were sent to us.

We hope that in reading them, you find the same comfort and joy we found in reliving our favorite memories of our Overland experiences.

Dan Gluck, an incoming member of our Support Staff, cycled through Canada– three times! After testing out the country on Nova Scotia and Acadia, he completed both sections of Canadian Rockies and Montana. He remembers a particularly meaningful Dessert Circle in Waterton Lakes National Park, just north of the US border. Dan reflects, “What makes this dessert circle so memorable was the turning point it signified in our short journey from Banff to Missoula. We had completed four strenuous days and we were geared up to do it again making a final push to the end.” What made that moment of rest so special? Dan thinks it was the ability to reflect: “We were able to recap our journey thus far, all the pain, the laughs, the hard work and the victories we had experienced throughout the ride. We got to take one last moment to relax before we resumed our trip. It was also bittersweet as it was our last day in Canada, which meant we were almost home, or at least back in the United States. Our Dessert Circle took place in one of the most incredible spots any Overland group could possibly find and that only adds to why it was so special! Just when it couldn’t get any better, we were greeted with a rainbow to cap off the evening.” Dan wants to give his cheers to those working on the front lines or staying home, “doing their part to ensure that more memories like these can be made down the road.”

Tyson Moose spent last summer hiking, kayaking, and rafting in New York and Vermont on North Country Adventure. While he says he had the “best time ever,” one of his favorite Dessert Circle moments was getting to let out a little energy on the monkey bars with his friends and leaders before settling down for quieter reflection time.

Margaret Fleischner remembers an especially great Dessert Circle from her Yellowstone Teton Expedition trip a few years back. Deep in the backcountry, their group had cooked cinnamon rolls for dessert– complete with icing! Though the mosquitoes were bad (no trip is perfect!), Margaret remembers this as one of her favorite Dessert Circles. “I don’t even recall most of the details of what was said at the circle, but I remember sitting around with great friends and a killer dessert and it was a memorable feeling​.” Three years later, Margaret is grateful to have made some incredible friends on that trip– and eaten some amazing desserts!

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