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.

The Certainty of Each Other

Teamwork & Leadership

Large group of staff gathered outdoors during training. View of the Berkshire Mountains in the background.

Meg Pritchard, a member of our year ’round team, shares some reflections on Overland in these unprecedented times.

At Overland, we have always embraced challenge. We have learned to cheer each other on, to give support, and to receive it, too.

These past few weeks have represented challenge outside of what we know. This is not a strenuous hike or a long bike ride, or even first-time-away-from-home jitters. These are unprecedented times, and it is natural to be anxious in the face of the uncertain and unfamiliar.

But at Overland we make the unfamiliar familiar. On the first day of a trip, seeing all of those new faces can be nerve-wracking. Just twelve days later, we may be crying because we’re leaving some of the best friends we’ve ever made. Packing our bags on the first day of backpacking may seem impossible—how can we ever hope to fit all that in there? But four days later, we’re packed up first and helping our friends. Our first nights of sleeping in tents might be something we’ve been worrying about for weeks, but soon enough, it’s something we look forward to: time in sleeping bags, whispering with our friends, dozing off together in warm summer air.

We can’t do this—the adjusting, the adapting, the accepting of the unknown—alone. That first day can be hard, but it’s made so much easier by our leaders, who show us how much they care, and by our peers, who reach out to build friendships. The first day of packing packs can be overwhelming, but we ask for help from our friends, and give it, too. Those first nights in tents can be stressful, but it’s those around us who make it fun. We learn that we can face challenges and confront uncertainties if we rely upon each other.

In our Williamstown office, we have been comforted by the love and support of the Overland community. From calls with our gracious parents to emails from our caring leaders, we are grateful to feel connected to you all. As we do our part and transition to remote work, we are thinking of all of you who are facing new, unfamiliar challenges at school, at work, or at home. Though we may be nervous about the unknowns that lie ahead, the Overland community is built upon the desire to support each other, to find in uncertain times the certainty of each other.

We’ve hiked past where we thought we could hike, carrying more than we thought we could carry. We’ve biked farther than ever before, and over hills that once would’ve seemed daunting. We’ve pushed—to the top of that mountain, to the crest of that pass—and seen the world open up around us.

New days may bring new challenges, but one thing is clear: our community is strong. As we look ahead to the coming weeks, we are grateful for everyone who is a part of our Overland family.

Meg Pritchard is a 2018 Yale graduate who led hiking trips for two summers before joining the Overland team as an Assistant Director of Trip Planning.

Filed Under: Teen Summer Adventures / Teen Adventure Travel

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