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.

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Annie Duryea

Assistant Director, Trip Planning

Email Annie

There was nothing more I wanted to do during my childhood than play outside with my siblings.

Being called inside – for dinner, bed, or any other reason – was one of my worst fears. My siblings and I loved to play in our backyard until it was too dark to see. I grew up in a magical little ski town called Crested Butte, in the heart of the Rocky Mountains, where I was lucky to hike, camp, ski, and, my personal favorite, mountain bike. I attended Colorado State University and majored in Integrated Visual Studies, where my senior project focused on food insecurity and its implications on childhood development.

I led New England Explorer and Appalachian Trail Expedition, and joined the trip planning team soon after. If I could piece together my dream job, it would look just like what I do now at Overland — creating an environment where we share challenges and triumphs of outdoor experiences with students. It is rewarding to watch our work unfold as we piece together trips and watch students discover the excitement and adventure that comes with an Overland experience.

As I design trips for Overland students, I’m fueled by my desire to share the same magic I felt in the outdoors throughout my childhood with our students. Our team is unique in that we not only get to share the outdoors with students, but also with one another as we adventure together outside of work. I am honored to be a part of the Overland team.