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.

Summer 2020: Hopefulness, Resilience & Optimism

Discovery & Inspiration

An idyllic picture of friends on this hiking trip for teens in New England

Friday, May 29, 2020

It is with deep regret that Liz and I canceled all of our 2020 trips on Thursday, May 14.

We want everyone to know how sorry we are—there is nothing we would like more than to welcome you into the Overland community this summer.

Every year, we have put the health and well-being of our students, our leaders, and our staff at the forefront of our decision making. This year is no exception. We have carefully monitored the guidance of public health officials. We have assessed the impact our groups would make on the communities through which they would travel. And we have thought carefully about the families our students and leaders would return home to at the end of their trips.

When we consider all of this, we know that, hard as it may be, canceling our trips is the right decision.

Liz and I look to the future with a hopefulness rooted in the resilience and optimism of the Overland community. The reflections here by Overland students, parents, leaders, and staff make us all the more eager to look ahead to brighter days.

The summer of 2020 will not be what any of us planned, but that doesn’t mean it won’t be meaningful. We hope that you and your family stay safe and healthy, and that you find ways to explore together, to discover again how beautiful and exciting, how full of promise the world is.

We thank you for your messages and calls. All of us at Overland are grateful for your support.

With our best wishes,

Tom & Liz Costley

Frequently Asked Questions

Can we sign up now for a trip for next summer?
Yes. The website is updated with our offerings for 2021—we’re excited to have something to look forward to!

Do any 2021 trips have limited availability?
Yes. Many 2021 trips have limited availability. Until June 1, 2020, we will give priority to our 2020 students.

If I’m a senior in high school this year, can I do a trip in 2021?
Yes! Please choose any trip open to students who will complete 12th grade next spring.

Will Overland’s 2021 enrollment be the same as previous years?
No. We expect to cap enrollment for many of our trips.

How can we contact Overland?
Email is best: info@overlandsummers.com.

Thank you for your support—we appreciate it.

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