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.

LB Headshot

Lilly Bianchi

Assistant Director, Leader Hiring

Email Lilly

I’m constantly surprising myself with new passions and adventures.

I’ve fallen in love with a lot of things: playing ice hockey, writing, bicycle touring, and, most recently, the Adirondack mountains. I’ll give almost anything a try because you never know when it will spark new excitement.

I’ve been lucky to have a constantly growing and evolving role at Overland. As a student, my experiences built the foundation for a love of challenge and the outdoors that carried me all the way to leader training here in Williamstown. For five summers, I led trips and worked on the operations team. Connecting with students and co-leaders to move through challenges and appreciate the world around us has been one of my greatest joys. I will never forget my students’ strengths. Watching them embrace every challenge with perseverance and wonder was incredible. To me, that’s the essence of Overland: to find joy in difficult moments because you’re surrounded by people who care.

I look forward to helping both leaders and students grow from their experiences with Overland and working with such a dedicated and compassionate team. Overland leaders have an amazing opportunity to inspire their students and I am so excited to help them feel empowered and prepared for their summer.