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.

Our Leaders

Far more than simply counselors or guides, Overland’s leaders are terrific role models for our students. Capable and caring, our leaders focus on creating supportive, wholesome environments where every student can flourish and grow.
A leader points out a hiking route to pre-teens on their summer adventure trip with Overland
Leaders plan activites for their campers this summer on an Overland adventure program Leaders and campers are friends on our summer adventure programs for teens
1000 applicants

We recruit our leaders from America’s finest colleges and universities, meeting with campus leaders across the country—an effort that generates hundreds of applications every year.

300 minutes

We typically spend over five hours evaluating our finalists: there are two readings of the application, a thorough review of three references, a three-part background check, and two rounds of interviews.

200 leaders

In 2022, over 200 individuals led for Overland. A mix of first year and returning leaders, our leaders include top students, athletes, and campus leaders—ideal role models for our students.

50 colleges

We recruit our staff from some of the country’s top schools and rely on our network of leaders at these schools to produce a deep pool of qualified applicants.

14 days

From extensive pre-summer preparations (first aid certifications, readings, and videos) to a demanding training session in Williamstown in June, our leaders invest fourteen days (minimum—for many leaders it's more) preparing for the summer.

1 goal

Our talented leaders have one goal: the success of each of their students. This, perhaps more than anything else, has made the difference for us as an organization and for the thousands of students who have joined us.

Become a Leader
for Overland.

Lead for Us