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.

Ben Banner e1537902124350

Ben Grannis

Assistant Director, Trip Planning

Email Ben

Since growing up in a small lake community in Ridgefield, Connecticut, I have preferred being outside over everything else.

I led my group of neighborhood friends on bike rides around our lake and on sledding trips down our snow-covered yards. I even organized a group to fix a patch of road near our elementary school. My love for the outdoors and working with others continued with my experience in Boy Scouts and strongly remains with me at Overland today.

Two of my good friends at Kenyon College whom I deeply admire led for Overland and praised all aspects of the organization — its structure, values, and experience for both leaders and students. As I thought about career prospects during my senior year, I saw Overland as a way to grow as a leader and to refine my skill set and interests. In 2017, I led Northwest Leadership in the gorgeous volcanic environment of Oregon and Washington with enthusiastic middle school students who were experiencing backpacking for the first time. In 2018, I was privileged to lead more experienced students who, at times, were encouraging me on steep uphills in the Spanish Pyrenees on European Expedition. Overland is an extraordinary community — having the opportunity to show kids the great outdoors and make an impact on their lives is a huge honor.

I am so excited to work with such a strong group of energetic and motivated people for the common purpose of helping young people get outside. Living in a community filled with beautiful wilderness and like-minded people is a dream come true.