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.

riley 1

Riley Thoman

Assistant Director, Operations

Email Riley

I grew up in Williamstown and first met Tom Costley when he coached my sixth grade soccer team at the Williamstown Elementary School. I don’t remember if we had a winning season, but I remember having fun and Tom calling me “The Thominator.”

Tom was a classmate of my father’s at Williams College so they have known each other since the 70s. My dad, Jay Thoman, is a Chemistry professor at Williams, and my mom, Lee Venolia, is on the Board of Berkshire Grown which supports and promotes local agriculture as a vital part of the Berkshire community, economy, and landscape. My younger sister is a senior at Smith College in Northampton, Massachusetts.

Four years ago, I did some work for Overland from home, and three years ago, I started to work in the office part-time. I enjoy working with all of the wonderful, friendly people in the office. Outside of work, I like playing board games and walking on Williamstown’s many trails.