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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Chris McAlister

Director, Operations

Email Chris

Organization is my middle name. From a young age, I enjoyed putting things in their place.

When I was eight, I would pull everything out of the linen closet and refold it all into neat color-coded and sized piles. In college, I folded for The Gap. After college, I had a brief stint as a home/closet organizer. My career path from there is quite varied, but in every position my organizational skills have come in handy.

I joined Overland just after moving to Williamstown from Boulder, Colorado. I wasn’t looking for a job, but there was something about the people and the energy that seemed like a good fit. I was immediately attracted to the collaborative atmosphere, and, of course, there were tons of organizational opportunities.

I love my job. I get to wear many hats, and I get to work with great people who are smart, thoughtful, and fun. I organize details, forms, numbers, and people.  I love finding the missing piece of the puzzle. To do all of that and work toward a goal that I believe in is really quite special. Being a parent makes me appreciate all the work we do even more.