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.

brenda 1

Brenda Briguglio

Assistant Director, Admissions

Email Brenda

I spent many childhood summers at my grandparents’ house on a lake in northern Michigan; I was lucky.

My days were filled with swimming, boating, horseback riding, hiking, and exploring on my own. The outdoors took care of me, and I loved the feeling at the end of the day as I nodded off to the sounds of the wilderness — so different from the sounds of the city during the school semester. In our Overland Poetry Book, we quote Jalil Al-Din, who wrote, “Let the beauty we love be what we do.” I love being part of a team that creates opportunities for students to discover what they love every summer.

I wanted to learn more about the service programs Overland offered so I walked into the office one day with a resume, and a friendly staff member told me to walk right into Tom Costley’s office and introduce myself. There was a staff meeting going on. However, everyone was so friendly and welcoming. That was the summer of 2006, and I started working for Overland that fall. I left Overland in 2009, moved to Hawaii, and then eventually returned to Williamstown in 2011; I’ve been here ever since.

I enjoy meeting and getting to know new Overland leaders and greeting our returning leaders when they arrive for Leader Training. They are engaged, excited, and dedicated young people. Many of the friendships I have made have continued over the years into graduate school, marriage, and even children — the Overland connection spans the entire globe. I love working with our incredibly hard-working, fun, energetic, and caring Admissions team and staff.