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.

Sarah Kravitz Banner

Sarah Kravitz

Assistant Director, Trip Planning

Email Sarah

Since I was young, I have loved everything about being a member of a sports team — the friendships it fosters, the responsibility it demands, and the collaboration it encourages.

In middle school, I had a hockey coach who pushed us to give 110% effort 110% of the time. I applied this approach to field hockey and lacrosse throughout middle school and high school, to rugby in college, and to my endeavors beyond athletics.

During the summer before my junior year of college, I was part of a team that planned Middlebury College’s first-year orientation trip program. I loved collaborating with a small group to create exciting trip itineraries that would, in many cases, be our new students’ first introduction to the variety of communities, landscapes, and outdoor activities that Vermont and the Champlain Valley have to offer. Then, at the beginning of my senior year, I led a first-year orientation trip with a dynamic, fun, engaging, responsible, silly, and inspiring co-leader, who was also an Overland leader. I knew that leading for Overland was exactly how I wanted to spend my summer after graduation. In 2016, I led Language & Hiking Spain; I loved experiencing a new place and culture with my co-leader and our incredible students. Overland trips allow students to learn from others, challenge themselves, test new waters, and create lasting friendships. I am so happy to be part of the Trip Planning team that creates trip itineraries that foster teamwork among our students.

As I approached my graduation from Middlebury, I couldn’t imagine not playing on a team for the first time in 13 years. However, since my first day in Williamstown, I have felt welcomed by Overland’s year-round staff. Not only do we collaborate and support each other in the office, but we play and explore together here in the Berkshires. I am so fortunate to work and live with such a passionate, committed team who works together and gives 110% to provide incredible, formative experiences for Overland students.