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.

Caitlin Beakes Banner

Caitlin Beakes

Hometown: Chevy Chase, Maryland
College: University of North Carolina at Chapel Hill

At the University of North Carolina, I was the captain of the women’s varsity rowing team and a four-year member of the Carolina Leadership Academy.

Originally from Chevy Chase, Maryland, I graduated from the University of North Carolina at Chapel Hill in 2018. I double majored in sport science and history and minored in Spanish. I rowed for four years, was a member of the UNC Student-Athlete Social Justice organization and completed all four levels of the Carolina Leadership Academy. I organized many community service events as the outreach representative for the rowing team. I was also on the ACC All-Academic Honor Roll for four years. Since graduating, I have been working as a WWOOF (World-Wide Opportunities on Organic Farms) intern at farms in California, Hawaii and abroad. I enjoy running, watching UNC basketball and petting dogs.

In 2018, I led Maine Coast Explorer, and in 2019, I led Norway Explorer. The highlight from my 2018 Overland summer was the night before we hiked Mount Katahdin. We had a dance party in the rain in Baxter State Park; we turned up our speaker really loud and danced around our campsite, not at all bothered by the rain.