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 for a summer outdoors with friends that's long overdue!

Please Join Us Next Summer!

Last spring, as we all started to come to grips with a changed world, one of our alumni described Overland as a gift. We couldn’t agree more. A gift to our students. To our leaders. To our staff. And, a gift to us. For thirty-seven years, we have been grateful to be a part of Overland, to feel the trust placed in us.

With our very best wishes,
Tom & Liz Costley

Our office is staffed Monday to Thursday from 8:30 to 7:00 EST, Friday from 8:30 to 4:30, and Saturday from 10:00 to 4:00. Please call (413.458.9672) or email (info@overlandsummers.com).

Current COVID 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

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