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.

Sophie Czerwinski Banner

Sophie Czerwinski

Hometown: Gilford, New Hampshire
College: Dartmouth College

After leading for Overland this summer, I moved to Lesotho, Africa, to work as an HIV/AIDs adolescent educator with the Peace Corps.

Originally from Gilford, New Hampshire, I graduated in 2019 from Dartmouth College with a degree in anthropology and global health. On campus, I joined the club Nordic ski and the club lacrosse teams. I was also involved with Directing Through Recreation, Education, Adventure and Mentoring as a student mentor and Planned Parenthood Generation Action as an activist. I worked at the Dartmouth Institute for Health Policy and Clinical Practice at Dartmouth Hitchcock Medical Center as a public health research assistant analyzing “Shared Decision Making” practices. During my sophomore year, I took a winter off to work at Gunstock Mountain Resort, teaching cross country ski lessons and leading snowshoe tours. For my junior winter, I lived in New Zealand and studied colonialism from an anthropological perspective at the University of Auckland. In my free time, I enjoy vinyasa yoga, running, skiing, and doodling.

In 2019, I led Berkshire Adventure. I had a wonderful summer working as part of the Overland team. I feel so fortunate to have spent 8 weeks working alongside such inspired, kind, diligent, and smart people. My students were constantly expressing disbelief at how close a group of strangers can become over the course of a mere week.