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.

Overland Summers Overland Summers
Overland Summers Overland Summers

Summer trips for
4th-12th Graders

Everyone at Overland is eager to get outside and explore this summer... please join us!

A Message from Overland

Our year ‘round team wants everyone in the Overland community to know that we are thinking of them during this extraordinarily difficult time.

There is nothing we want more than to provide each of our students with the kind of summer that brings the life-affirming joy of new adventures and new friendships.

We continue to hope that we can do this. Our trips are planned. Our leaders are ready. We are eager for the summer. But for now, all we can do is wait a bit longer in the hope that an Overland summer, a summer outdoors with friends, will happen again in 2020. We ask all of our enrolled families to wait with us. To make that possible, we have moved our final payment deadline to Wednesday, May 6th.

This means that all deposits and final payments are fully refundable until May 6th.

While we wait, most of our team will be on what we hope is a temporary furlough, and the Overland office will be staffed remotely by Emily Ferrell and Chris McAlister. Emily and Chris are available via email (info@overlandsummers.com). Please reach out to them with any questions or concerns you might have.

For the past thirty-five summers, Liz and I have marveled at the power of the Overland experience to nurture and inspire everyone who is a part of it—us, most of all. We are committed to doing everything we can to make that happen again this year.

Best wishes,
Tom & Liz Costley

Far more than simply a summer experience, Overland is a life experience with value and resonance that extends far beyond the boundaries of a single summer.

In everything we do, we seek to inspire our students to see how beautiful and exciting, how full of promise the world is. Each of our trips offers carefully crafted itineraries, small groups, and capable, caring leaders. Our adventures are many: hiking, biking, kayaking, rafting, climbing, and more. And our destinations include some of the world’s most beautiful mountains, coastlines, and countrysides. But Overland is more than exciting activities, more than great destinations. Overland is a chance to step out into the world on your own, while sharing in the friendships and fun of a small group with terrific leadership.

Our Trips

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Take The Journey

Learn About Overland


Our Story

A bike, a small group of friends, and the span of a whole country disappearing beneath his tires instilled a desire in Tom Costley to provide similar growth experiences to youth.

Learn More about Us
Tom Costley cross-country biking trip 1982
Utah 1982: Tom Costley, Ralph Blasey, and a Swiss friend

Our Values

Teamwork & Leadership

In a pivotal stage of my life Overland was there to teach me how to become a leader. – Corey Schwitz

Independence & Self-Reliance

We felt Jackson would benefit from an experience that promoted independence. We wanted him with good kids and inspiring leaders so he could grow. – Margaret Cooper

Discovery & Inspiration

Overland teaches reverence, respect, and appreciation for the natural world. Jane considers sunrises and sunsets, the stars, beaches and mountains and forests and plains, even the wind, in a completely different sense than she did before her Overland summers. – Helen Hamel

Our Commitments

Learn more about our commitments and what matters to us.

  • Financial Aid & Scholarship Program Available
  • Committed to a Healthy Sustainable Planet
  • Committed to Giving Back
Here's What Matters

Why Overland

Keep your eyes peeled while hiking on a teen adventure program with Overland
Our Leaders

Overland’s leaders are terrific role models for our students. Capable and caring, our leaders focus on creating supportive, wholesome environments where every student can flourish and grow.

Meet Our Leaders
Teens take a summer kayaking trip on an adventure program with Overland
Our Small Groups

Our groups are limited to 12 students — we pay attention to age, grade, gender, the mix of hometowns and schools, and we limit friend pairs to no more than two per group.

Why Small Is Better
Group gathers around a craggy mountain face while on a summer hiking trip with Overland
Our High Standards

We expect a lot of our students — from playing by the rules to including everyone and helping out. At Overland, we value a positive attitude, enthusiasm, and consideration for others.

High Standards Matter