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.

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Nate Greason

Assistant Director, Trip Planning

Email Nate

As a kid in the gorgeous Pacific Northwest, I was constantly in search of new adventures.

I’d beg my parents to let  me go on adventures in the woods behind our house each afternoon before dinner. In the summer, I explored Puget Sound via kayak; in the winter I’d count down the days until the next weekend we were planning on driving up to the Cascades and going skiing.

Since those early days, outdoor adventures have fostered countless meaningful moments of personal growth for me. I spent my first weeks away from home at a summer camp in Northern New Hampshire, and I made lifelong friends on my orientation trip at Dartmouth College. Then, my three summers leading trips for Overland strengthened me as a leader and pushed me to be the best version of myself each morning, as my groups and I prepared to tackle the day ahead.

I love each time I can share the adventure of an Overland summer with someone new. Each Overland trip represents a truly unique opportunity to go on an adventure in an amazing location, to share life-changing experiences with new friends, and to grow as a leader. I am lucky to be a part of the amazing full time team, and cherish my role facilitating fantastic experiences for our students.