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.

TS Headshot

Torie Smith

Assistant Director, Admissions

Email Torie

Growing up in the Berkshires, being outdoors was a way of life.

The woods behind my house was my playground, a ski mountain was minutes from my home and my quickest commute to friends was on the bike paths across the mountain.

As a local student, it was a thrill to be given the opportunity to go on three Overland trips. Whether biking from my hometown to Montreal, hiking in the Rockies, or exploring along the Pacific Coast, each Overland experience, no matter how unique, held the constant of building a foundation of confidence, community, and adventure. They remain formative experiences in my life.

After a decade of work in the boarding school community, I feel so lucky to come full circle back to Overland. I love working with students and families in their quest for what I know to be a remarkable opportunity for growth, exploration, and independence, and feel honored to be a part of such an exuberant and impressive team.