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.

Summer 2022: Admissions Update #3

Discovery & Inspiration


Here in Williamstown, we’ve been enjoying the buzz in the Overland office as we work with families to find trips that are a great fit for their children. Trips have been filling faster this year than in any past year. We’re glad that students are eager to get outside for another fantastic Overland summer! We’re already looking forward to a summer filled with new friends, gorgeous sunrises and sunsets, laughter, singing, and storytelling. 

Photo Jul AM
Middle schoolers enjoy a bluebird day in the mountains of Maine.

Visit the Overland website and look at the icons next to each trip (available, limited, and waitlist) that indicate availability. We work with each family, though, to find the best fit for their child. We want to make sure there are students of the same age in a group, and that it’s a great mix of kids from across the country. We do our best to have the website reflect available space, but cannot guarantee a spot on a trip until we receive and carefully review each child’s application. To know more, please reach out to us: info@overlandsummers.com.


Introductory trips are a great option for our youngest students to challenge themselves!

One of our students once described Overland as a gift. We couldn’t agree more: a gift of adventure and exploration, of friendship and fun. Join us next summer, and see for yourself the gifts Overland offers you. 

Feel free to contact us anytime (413-458-9672) to discuss trip options—we’re always happy to chat!

Photo Jun AM X
American Challenge bike leaders stand in the Santa Monica surf after successfully leading their group across the country.

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