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.

Molly Gallagher Banner

Molly Gallagher

Hometown: Wilmette, Illinois
College: Middlebury College

As a student, I participated in six Overland trips — Sierra Adventure, Northwest Explorer, Yellowstone Teton Explorer, Alaska Explorer, Appalachian Trail Challenge and the Alpine Challenge; Overland made me the person I am today.

Originally from Wilmette, Illinois, I am a sophomore at Middlebury College where I study political science and sociology. In high school, I was a distance runner, and now, I am a member of the Middlebury Lady Pranksters, the ultimate Frisbee team. I like to take full advantage of Middlebury’s proximity to great skiing and plan to continue exploring local mountains for both skiing and hiking. One of my favorite things about Overland is the way that the group comes together while preparing and sharing meals, and I do my best to recreate that atmosphere in the dining hall at Middlebury. In my free time, I like to hike, work out, and listen to podcasts.

In 2019, I was on Support Staff and led New England Adventure. My favorite part of working for Overland is getting to facilitate a fun and challenging experience that builds confidence and independence for my students, like my leaders did for me.