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.

May 2020 FAQs

Thank you for your support! Please see our FAQs below.

Can we sign up now for a trip for next summer?
Yes. The website is updated with our offerings for 2021—we’re excited to have something to look forward to. If you enroll before June 1, 2020, we will provide a $200 credit toward your trip as a thank you for your support.

Do currently enrolled students have to reapply for 2021?
No. Just indicate your preference on the family portal and email us your trip and departure date choices.

Do any 2021 trips have limited availability?
Yes. Many 2021 trips have limited availability. Until June 1, 2020, we will give priority to our 2020 students.

If I’m a senior in high school this year, can I do a trip in 2021?
Yes! We welcome your participation in 2021. Please choose any trip open to students who will complete 12th grade next spring.

We see that you’ve made changes to your offerings for 2021 — why is that?
Every year we add and drop trips, and revise and restructure others. This year is no different as we continually improve our offerings.

Will Overland’s 2021 enrollment be the same as previous years?
No. We expect to cap enrollment for many of our trips.

We are enrolled for this summer; if we put our 2020 payment toward a 2021 trip, is it refundable?
Yes. Your 2020 payment is fully refundable until March 1, 2021.

We’ve paid our full 2020 trip fee, can we leave just part of it as a deposit for 2021?
Yes. If you’d prefer to leave a deposit of $795 instead of your full 2020 trip fee please indicate this on the family portal.

Did Overland consider alternatives for this summer?
Yes. From the beginning of the pandemic, we have searched for ways to make our trips possible. We have considered every reasonable alternative—from delaying the start of our trips, to reducing group sizes, to offering just a few trips close to our home in Williamstown. In the end, we have come to recognize that there is no responsible way to move forward with our trips.

Can Overland survive a summer without trip fees?
Yes, Overland will be fine. We are fortunate that our financial situation is secure.

How can we contact Overland?
Email is best: info@overlandsummers.com.

Thank you for your support — we appreciate it.