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.

WS Headshot

Will Savage

Assistant Director, Leader Hiring

Email Will

I have always loved stories.

It doesn’t matter if I am listening to, reading, watching, or telling stories, but I have found that my favorite stories always involve being outside. I don’t know why this is, perhaps it’s the element of adventure or the feeling of being in the “wild.” Most likely it’s that adventures outside are almost always shared with friends, both new and old.

When I was younger, I was lucky enough to go camping once a month with a group of neighbors and friends, where being potty trained was the only qualification. Since then I have spent many weekends exploring the Texas Hillcountry by kayak and canoe. More recently, I spent my time in college exploring the forests and mountains of Maine, leading trips through the Bowdoin Outing Club. The best part of all of these experiences was the opportunity to explore new places while learning new skills and making friends along the way. One of those friends happened to tell me about Overland in 2020 and I jumped at the opportunity to share my enthusiasm for the outdoors with others. In the following summers, I led Alaska Explorer and Sierra Expedition before starting full-time in the office.

Working in Leader Hiring, I am excited to introduce new leaders from all different walks of life to the Overland community. I have seen firsthand how incredible summer with Overland can be and can’t wait to help other leaders and students experience it.