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.

Trevor Cook Banner

Trevor Cook

Hometown: Mechanicsville, Virginia
College: University of Virginia

Last summer, as a horse wrangler at a camp in Colorado, I felt great joy witnessing my campers’ excitement as they learned how to ride horses on the beautiful Rocky Mountain trails.

Originally from Mechanicsville, Virginia, I am a mechanical engineering student and a senior at the University of Virginia. I’m on the snowboard team here, so in the winter, I spend every weekend and many weeknights snowboarding in Virginia or North Carolina. I’m also a part of Young Life College, a Christian ministry for college students. In my free time, I like to play sports with friends, go on hiking trips, take spontaneous road trips, or read a good book. On a beautiful day, I enjoy playing Spikeball or volleyball on the Lawn at UVA for hours.

In 2019, I led Rocky Mountain Explorer. Overland has a culture of kindness and selflessness. Whether it was helping encourage a student to complete Mt. Elbert, our challenge hike, or helping students develop their independence around camp, I enjoyed each moment I spent with my groups.