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.

Andy Ballard Banner

Andrew Ballard

Hometown: Larchmont, New York
College: Yale University

In high school, I spent my summers in a small Maine fishing town, where I hiked the mountains of Acadia National Park and taught sailing classes on the magnificent waters of Frenchman’s Bay.

Originally from Larchmont, New York, I’m a senior at Yale University, where I study English. Outside of class, I’m the co-coordinator for Yale’s first-year outdoor orientation program, for which I lead backpacking trips across New England and help first-year students acclimate to college. I’m also the editor-in-chief of Yale’s travel journal, a captain of the school’s club running team and a baritone in the Yale Glee Club — the university’s oldest singing ensemble. In the summer after my freshman year, I studied abroad in Paris, immersing myself in the French language and picnicking in the city’s beautiful parks. I’m an avid fan of cycling, trail-running and hiking. When I’m not outside, you can find me exploring an art museum, working Yale’s vintage printing press or diving into my favorite anthology of short fiction.

In 2019, I led Writing and Hiking New England. As we neared the end of one of our trips this summer, we hiked Mt. Greylock in a torrential downpour like no other. The skies opened right as we hit the trail, and we were immediately drenched. Remarkably, our students pushed on—not only tenaciously, but enthusiastically. I’ll never forget the sound of laughter echoing through the woods as trees dripped with rain, and the incredible joy we all shared as we reached the peak, sopping wet and singing ‘Ain’t no mountain high enough.’  Writing and Hiking  New England was an invaluable opportunity to interact with a range of young people both through their writing and our shared outdoors adventure.