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.

Robert Denniston Banner

Robert Denniston

Hometown: Birmingham, Alabama
College: Yale University

In New Haven, Connecticut, I am involved with the Yale Restaurant Rescue Project, where I manage food donations from restaurants to shelters and teach local children basic cooking skills.

Originally from Birmingham, Alabama, I am a senior at Yale University where I am the captain of the club alpine ski team and a member of both the club lacrosse team and the Christian Union at Yale. As a history major seeking a certificate in energy studies, I study the ways in which people and society interact with their environment and natural resources. In my free time, I like to stay active through trail running and skiing. I also enjoy playing piano, as well as cooking — and eating — comfort food.

As an Overland student, I participated in Alaska Explorer in 2014 and Alpine Challenge in 2015. In 2017, I led New England Adventure; in 2018, I led New England Explorer; and in 2019, I led Swiss Alps Explorer. Without a doubt, the highlight of my summer was watching my groups grow and mature, not only as lovers of the outdoors, but more importantly as a family. As a leader, the most rewarding thing is to be able to step back at the end of the trip and watch as your group takes care of itself.