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.


Julia Chenail

Assistant Director, Admissions

Email Julia

Becoming a mother drew me back to the Berkshires

Having grown up in the Berkshires at the base of Mt. Greylock, I have been able to experience the sheer beauty that the area has to offer from all angles. Spending hours on end exploring the forest and trails, to crafting lean-tos in my backyard, I grew up embracing nature.

My love for the outdoors continued as college pulled me to New Hampshire where I skied competitively and explored the White Mountains. For me, getting outside and being able to move freely is so invigorating. Throughout my life, I have participated in team sports and I’ve been given the opportunity to experience a multitude of adventure-based trips. These challenges helped me learn my strengths and weaknesses, and find my courage.

I wanted to give my children the same freeing experiences surrounded by nature that my parents were able to give me. I feel honored to be a part of the Admissions Team at Overland and am fortunate to work with others who are so passionate and motivated. The Overland Team is a dedicated group working together to accomplish one goal: helping students find their next adventure.