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.

Looking Back, Looking Forward: Hopefulness, Resilience & Optimism

Discovery & Inspiration

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

October 2020

We can’t wait to get outside with you!

The Overland team is planning, preparing, and eagerly awaiting Summer 2021. While we can’t predict what the next year will bring, we do know how we will face it: together

That’s why we are—as always—prioritizing health and well-being by basing all of our decisions on the best public health information.

And, to allow families flexibility in the face of continued uncertainty, we will make all payments fully refundable until April 1.

We look forward to having you with 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 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.

Given the ongoing uncertainty around COVID-19, are deposits for next summer refundable?
Yes. All payments are refundable until April 1, 2021.

How can we contact Overland?
Call (413.458.9672) or email : info@overlandsummers.com.

Thank you for your support—we appreciate it!

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