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.

Our Story

For nearly forty years, Overland has been more than simply a summer experience

— it’s a life experience with value and resonance that extends far beyond the boundaries of a single summer. In everything we do, we seek to show our students how beautiful and exciting, how full of promise the world is.

Having just graduated from Williams College, Tom Costley was inspired to offer experiences to kids with a focus on small groups, carefully crafted challenges, and clearly defined goals. In 1984, Overland became a reality with three trips in New England. In the decades that followed, new destinations and activities were added but a common mission remained: to provide young people the chance to work together in small groups to accomplish something of importance to them—hike the world’s most beautiful mountains, work with an underserved community, master a new language.

Almost forty summers later, Overland has grown wonderfully but remains true to its original inspiration. Rock-solid values—teamwork and selflessness—imbue an organization where the standards are high, the expectations clear, the tone adventurous.

Learn More About Us

Office Photo
Meet Our Team

Learn more about the people who work year-round to provide life-changing summer trips.

Meet Our Year 'Round Team
Friends pose for a photo while on their hiking adventure trip with other teens in the Sierras
Our Commitments

Learn more about our commitments and what matters to us.

Learn More About Our Commitments
Teens take a summer kayaking trip on an adventure program with Overland.
The Overland Difference

Learn more about what we love about Overland.

Learn About What Makes Us Different