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.


Dave McCahill

Assistant Director, Trip Planning

Email Dave

For my fourth birthday, my parents invited my friends to join me on a bike tour to the neighborhood park and back.

My steed was a three-wheeled plastic John Deere tractor and my gear list included a helmet, two crayons, and a gumball. While we were out riding, our yellow lab ate my entire chocolate cake, complete with mocha frosting. But during the ride, I learned that a great adventure shared with good friends is even better than homemade birthday cake.

I led my first trip with Overland in 2012. Since then, I’ve had the opportunity to lead students to the summit of Wyoming’s Grand Teton, alongside towering glaciers on the shoulder of Mt. Blanc, across knife-edged peaks in Norway’s Jotunheimen National Park, and through the wildflower-filled meadows along Switzerland’s Haute Route. Watching a group of students share the highs and lows of a summer spent outside is one of the most rewarding experiences imaginable.

It’s a pleasure to work here at Overland alongside colleagues who take such joy in being outdoors, and in sharing that passion with their students.