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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Conor O’Brian

Director, Leader Hiring

Email Conor

Growing up, my family moved around quite a bit — from California to Pennsylvania, Hong Kong to New Hampshire, and, most recently, to Maine.

These transitions, while challenging, showed me how beneficial it can be for a person to step out of his comfort zone. Repeatedly finding myself in different places surrounded by a new group of people helped me become confident in who I am. I learned to embrace the concept of leaving behind the securities of home in order to throw myself into unfamiliar situations. This inspired me to study abroad on three separate occasions during college, including spending the final two years of my undergraduate career completing my degree overseas in Wales. Now, I’m lucky to work on the Overland team, where my primary role is to find great leaders to facilitate fun, enriching, and rewarding summer experiences for each of our students.

During my high school and early-college summers working as a lifeguard and swim instructor, I discovered that I loved working with kids. I was searching for a way to combine this interest with my appetite for adventure, and during my junior year at Bates College, I saw an Overland poster in the dining hall. That evening, I applied to become a leader. I led trips for three incredible summers, and then I joined the year-round staff in Williamstown in the fall of 2016.

There is no better collection of people with whom to work and live than the Overland staff. Each person in the office shares the same determination to help create unforgettable adventures for kids, and no stone goes unturned as we prepare for the summer. The result is the Overland experience that I came to love as a leader, and now I get to help perpetuate that experience for future leaders and students.