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.


Emily Ferrell

Director, Admissions

Email Emily

As a child, most nights before falling asleep I would gather my stuffed animals in a circle on my bed to recap the day.

While I didn’t know to call it dessert circle yet, the tradition was important to me even at the age of five. On an Overland trip, I love taking time at the end of each day to reflect with the group and check in as a whole. It’s a wonderful opportunity for the entire group to spend time decompressing, listening to one another, and getting ready for the next day’s adventures.

My roommate at Pomona College led for Overland following her junior year. She returned to campus in the fall full of incredible stories about her students, her co-leader, and Overland. After seeing the transformative impact leading had on my roommate, I knew I wanted to be a part of Overland. I started leading for Overland in 2007; during the four summers I spent as a leader, I had the opportunity to bike through fields of sunflowers and over mountain passes in Europe with inspiring students and co-leaders. I also led two bicycle trips across the United States, sharing laughter, celebrating triumphs, and overcoming challenges with determined and strong Overland students. Some of those students have gone on to lead for Overland and are close friends. Leading for Overland was more challenging and simultaneously more rewarding than I had ever imagined. It’s difficult to describe the incredible amount of growth and leadership that develops over the course of an Overland trip — in students, leaders, and the group.

The people at Overland — families, students, leaders, and the year-round staff—are what make the organization so wonderful.