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

Join us in 2021 for a summer outdoors with friends that's long overdue!

Looking Ahead to a Healthier World

As we make plans for a summer without trips, Liz and I look back with a deepened appreciation for all of the opportunities we have enjoyed for so long.

We encourage you to join us as we look ahead. First to this summer, and to the new adventures we will all have. And, then, beyond the summer, with hopefulness that schools will reopen, that art, music, and sports will resume, and, most importantly, that by the time of the holidays, we will all be celebrating a healthier world.

Thank you for your many messages of support—we are grateful to be a part of this wonderful community.

With our best wishes,
Tom & Liz Costley

Although the Overland office is closed this summer, we will check our email regularly (info@overlandsummers.com), and we will continue to accept applications for Summer 2021!

Summer 2020 Message
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
Overland's founder Tom Costley on a summer bike trip in 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

The group goes on a hiking trip while on a teen summer adventure.
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
Teen hiking group gathers around a mountain on a teen summer adventure
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