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.

Hannah Benson Banner

Hannah Benson

Hometown: Jackson, New Hampshire
College: Williams College

Over the past two years, I have competed in ski marathons across France and Spain as a member of local ski clubs.

Originally from Jackson, New Hampshire, I graduated from Williams College in 2017 with a degree in French and comparative literature. At Williams, I competed on the Nordic ski team and was an active member of the Williams Outing Club through which I directed an outdoors program at the local elementary school. When I was not exploring the beautiful Berkshires, I was busy pursuing academic interests at Williams and abroad. My junior fall, I studied in Grenoble, France, and following graduation, I won a Fulbright scholarship to teach English in Andorra. I taught primary and secondary school English in a small village in the French Alps and now am working toward my Masters while living in Strasbourg, France. I enjoy cooking, trail running and taking advantage of the hundreds of kilometers of nearby ski trails.

In 2019, I led Language and Hiking France. One of my highs this summer was a cold and rainy hike up to a refuge during a wet camping weekend. I was really proud of and impressed by our kids’ positive attitudes despite the less than ideal conditions. I witnessed how the outdoors can bring any group together.  I am excited to continue to share my passion for the outdoors with Overland students, and I look forward to learning and growing alongside them.