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.

Leader Applicant Info Sessions

Join us to learn more about Overland, our leaders, and how to apply!

We are so excited that you’re interested in applying to be a leader for Overland! In a normal year, our Leader Hiring team would be travelling to college campuses all around the country to meet prospective leaders. Due to travel restrictions associated with COVID-19, all of our recruiting for 2021 will be conducted virtually, including our Info Sessions.

Please fill out the form below to RSVP for one of our Winter Info Sessions. We highly encourage anyone who is applying to attend one of these Info Sessions to learn more about Overland and hear from past leaders about their Overland experiences.

Once we receive your RSVP, a member of our staff will send you a confirmation email. You will also get a reminder email (including a link to a virtual meeting) on the day of the Info Session you plan to attend. If you cannot make any of the listed dates/times and would still like to learn more about Overland, please reach out to our Leader Hiring team at hiring@overlandsummers.com or call our office at (413) 458-9672.

Leader Info Session RSVP