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.

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Summer trips for
4th-12th Graders

Enrollment for 2023 is open! Let the adventures begin!

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.

Carefully Crafted Trips
Every Overland trip offers friendship and fun, laughter and stories, adventure and exploration. With carefully planned itineraries, thoughtfully calibrated challenges, and clearly defined goals, our trips capture our students’ imaginations, stretch their abilities, and strengthen their bonds with one another.

A World Full of Promise
Optimism. Enthusiasm. Joy. That’s what you see and hear and feel at Overland. In everything we do, we seek to inspire our students to see for themselves the world’s beauty and promise.

More Than Just a Summer Experience
Whether it’s a lifelong friendship, a trove of joy-filled memories, or a spirit-sustaining love of the outdoors, Overland is more—much more—than just a moment in a young person’s life.

Please join us!


Our Trips

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Take The Journey

Learn About Overland


Our Story

Four decades of fun, friends, and adventure.

Learn More about Us
Group of teens take a photo in the French countryside while on a language and hiking trip this Summer

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