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.

Hopefulness, Resilience & Optimism

Discovery & Inspiration

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

September 2020

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

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 was no exception. We carefully monitored the guidance of public health officials. We assessed the impact our groups would make on the communities through which they would travel. And we thought carefully about the families our students and leaders would return home to at the end of their trips.

When we considered all of this, we knew that, hard as it was, canceling our trips was the right decision.

Throughout what’s been a difficult time for us all, our spirits have been lifted by 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.

And now, here we are in September, with our plans made for next summer—plans rooted in our commitment to our students’ health and well-being, as well as their need for a deep connection to others and the outdoors.

Please join us next summer!

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 already have limited availability because so many of our 2020 families rolled over their applications to 2021.

If I was a senior in high school this past 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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