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.


Chelsea Colby

Assistant Director, Admissions

Email Chelsea

I’ve always been passionate about getting students outdoors.

During my time at Middlebury College, I fell in love with the community in Addison County, Vermont. After graduating, I began my teaching career at a local elementary school where I was the school’s beekeeper and loved taking my students out snowshoeing and Nordic skiing. During winter weekends, I taught alpine skiing to students of all ages at the Middlebury College Snow Bowl. As a teacher, I spent my summers seeking adventures throughout New England including thru hiking the Vermont Long Trail and the New Hampshire Cohos Trail.  In subsequent summers, I was looking for a way to bring my passions together and Overland was the perfect match – teamwork, discovery, and sustainability. In the summer of 2022, I had the incredible opportunity to lead Rocky Mountain Expedition and in 2023 I returned to lead Service and Hiking Alaska.

As a teacher and a leader, I love to experience the intense and wonderful power of immersive outdoor experiences and the ways they invite us to grow as individuals and bring us together in community. I’m thrilled to join the Overland year-round team where I can develop relationships with families and cultivate these inspiring and empowering experiences for students.