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.

Jonah Boucher Banner

Jonah Boucher

Hometown: Rochester, New York
College: Hamilton College

I’m best known to my neighborhood as the guy who loads a paddleboard onto his car whenever the temperature breaks 50°.

Originally from Rochester, New York, I graduated in 2017 from Hamilton College, where I majored in math and environmental studies. At Hamilton, I spent a lot of time on the ultimate Frisbee field, working alongside my twin sister as three-year co-captains. I frequently made the quick trip up to the Adirondack Park to hike with the outing club, paddle for the Marathon Canoe Racing Team or to study local history and culture as a leader for the freshmen orientation programs. I found time to study, too; I wrote a thesis on lake microbiology, spent a semester researching birds in Costa Rica and finished first in my class thanks to a deep passion for learning and incredible professors. After graduating from Hamilton, I worked as an AmeriCorps volunteer teaching high school math and science in Chicago, and currently, I teach math at a school in Waltham, MA.

In 2019, I led High Sierra Expedition. The highlight of my summer was a snowball fight we had in the middle of the Emigrant Wilderness during our backcountry. During that break during our day of hiking the only thing that mattered in the whole world to us was the fun we were having together.