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.

Berkshire Adventure

A terrific first trip!

With a wide range of fun outdoor activities, Berkshire Adventure is a great place to start!

Nestled in the northwest corner of Massachusetts, the Berkshires offer an inviting landscape of hills and mountains, rivers and lakes. Across the region, small towns dot the countryside, offering a look into a quieter way of life. As with every Overland trip, Berkshire Adventure offers a supportive, wholesome setting and caring leaders. Every day, the focus is on having fun and making friends — and getting used to adventuring away from home. A week of hiking and fun in the beautiful Berkshires: Come explore with us!

Download the
Berkshire Adventure Itinerary
for all of the details!
"I want to thank my leaders and the kids in my group for making this week one of my favorites. I am already thinking about which trip I want to do next year. Overland is so fun! "

Colette B.


"Best camp ever! He came home and said, "we should camp on our next vacation". I feel like it was life-changing, especially for a city kid! "

Jennifer S.