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.

Team leader, teen summer biking trip

Jordan Averill

Hometown: Dedham, Massachusetts
College: Colorado College

The fall semester before I started college, I lived in Nepal for three months where I enjoyed homestays, learned Nepali and backpacked in the Himalayas.

Originally form Dedham, Massachusetts, I am a junior at Colorado College. At CC, I teach Pilates classes at the gym and knitting classes as an arts and crafts adjunct. I am also a co-chair of the farm club; we organize farm work days where we either harvest, weed or do general maintenance on the farm. Also, I have danced in two student-run dance shows called Dance Workshop. Last fall, I completed the level one outdoor leadership training at CC and am now able to lead and create day trips or co-lead overnight backcountry trips. During my free time, I enjoy hiking, running, knitting, weaving and making dinner with friends.

In 2018, I led Berkshire Adventure. I am excited to lead for Overland because I love working with students and sharing my love for the outdoors with them. Our students understood that overcoming a challenge together can be fun — hiking Mt. Greylock, the tallest mountain in Massachusetts, was a high on each of my trips.