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.


Luke Costley


Email Luke

I’ve always loved rhythms and routines.

And the rhythm and routine of Overland has always been a part of my life. I feel so grateful to have grown up around Overland leaders, to have known the seasonal excitement of trips going into the field, and to see the joy and accomplishment at the end of each summer.

As a teenager, I went on three trips, hiking in the Rockies and Sierras, and riding my bike across the country. During college, I led for three more summers and cherished the months dedicated to building group experiences with my co-leader, living intentionally, and being outdoors. In my work since graduation from Williams, I’ve sought out opportunities that mirror the challenge and engagement of an Overland experience. I taught high school English in New York City for two years, and then split my time coaching Nordic skiing and working on a farm in the Upper Valley of New Hampshire. In each setting, I found the demands to be commensurate with the sense of satisfaction. The work allowed me to set clearly defined goals and pursue them with enthusiasm. It also pushed me to consider my own strengths and weaknesses, my blind spots and misconceptions.

As I’ve lean into the next chapter of my life at Overland, I’ve loved engaging in those same tasks, and valued, above all else, working alongside my teammates, our leaders, and our families to help them enjoy the promise of a summer with Overland.