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.

Open Arms: Broadening Access to Overland

Financial Aid

Financial aid is awarded in April and thereafter on a space-available and funds-available basis. Awards typically range from 10% to 50% of the trip fee. Most first-year financial aid students join us on trips starting in Williamstown, Massachusetts — this stretches our financial aid dollars, and makes it easy to lend equipment and bikes. Though we strive to meet the needs of all interested families seeking financial aid, we cannot guarantee an offer. When a financial aid award is offered and accepted, a non-refundable deposit is due.

Families can submit a financial aid application here. 


We are committed to building partnerships with foundations and schools. We work with Beacon Academy, Cristo Rey School, The Ellie Burns Foundation, Mile High 360, The Squash and Education Alliance, the National Cathedral School, Saint Ignatius Loyola Academy, Success Academy, Mount Anthony Union Middle School, and Herberg Middle School, and we look to add new partners each year. Many of our scholarship students receive 50%-75% financial support from Overland. In some cases, our generous partner organizations contribute to the cost of the trip, reducing the expense for families further. Overland is also able to assist some scholarship students with gear and transportation, as well as assistance through the enrollment process. If you would like to talk with Overland about setting up a partnership, please email our admissions team at info@overlandsummers.com.

The Overland Summers Foundation

The Overland Summers Foundation, a 501c3 organization, welcomes gifts from all members of the Overland community. 100% of every dollar received directly benefits scholarship recipients. Mail your check (made out to The Overland Summers Foundation) to our foundation administrator, Chris McAlister, at Overland, P.O. Box 31, Williamstown, MA 01267. Thank you!

Financial Aid Application

Submit a Financial Aid Application.

If you have any questions, please contact our admissions team at info@overlandsummers.com.