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.

MW Headshot

Marisa Wesker

Assistant Director, Admissions

Email Marisa

Growing up in an “indoor” family, my folks always ask me what Overland is, exactly.

It’s difficult to describe to them the transformative experience Overland provides – for students and leaders. To me, as a leader and now a year-round team member, Overland is ephemeral; it is a feeling. It is the feeling of waking up in the early morning half-light in Yellowstone with nothing to hear but the birds and the sound of your own breath. It is huffing and sweating your way to the top of a 14,000-foot peak in the Sawatch Range of Colorado’s Rocky Mountains, cresting the summit with eleven of your peers cheering you on, genuine love and excitement in their eyes. It is pure, uninterrupted joy. This is what brought me to Overland, and what brings our students to us from all over the world. It is the promise of an opportunity for growth, camaraderie, a challenge, and the chance to breathe fresher air and sink deeper into understanding oneself and others.

I have always drawn inspiration from walks in the woods, and I love being able to give students that same opportunity. I led Writing and Hiking New England in 2018 and Yellowstone Adventure the following year. Waking up to the Tetons as the mountains reflect the early morning light, seeing the sun rise on Yellowstone lake, and trekking our way to the top of 10,000-foot peaks, I fell in love with the big skies and thin air of the Rockies. I moved to Colorado after I graduated from Tulane University in New Orleans, Louisiana with a dual degree in Political Science and French.

While living in Colorado, I worked on an educational ranch near Rocky Mountain National Park – teaching middle school science – and I was also a ski and snowboard instructor. I now work on our admissions team in Williamstown. I’m thrilled to be part of Overland year-round and am so grateful for all Overland has given me.