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 2022: Admissions Update #1

Discovery & Inspiration


Over the past few years, we’ve been tremendously grateful for the outpouring of support from the Overland Community. This year is no different.

Students celebrate at the top of Mount Greylock.
It has already been a busy year for the Admissions Team! Since we launched the summer 2022 application in August, we’ve seen record enrollment for this year. Kids are eager to get outside and are looking forward to spending one, two, three (even six!) weeks amongst new friends. We’ve heard from parents who are excited to give their children the chance to get outside, away from screens and devices, and have fun with peers. We’re receiving more applications than last year, which was already a record year for us. While we’re grateful for the excitement for the summer (we’re also counting down the days until the summer!) – it does mean that trips are filling even earlier this year.
Currently, several trips are completely full, with many others near capacity. Kilimanjaro Expedition is full, and other trips abroad such as Alpine Challenge, Norway Expedition, Iceland Expedition, and Explorer, and Language & Hiking France have limited space. Domestically, Alaska Expedition, American Challenge, Yellowstone Teton Explorer, and Cape Cod are nearly full.
Photo Jul PM
Sea kayaking on Service & Hiking Alaska
Our 2022 catalog will arrive in homes just after the holidays. We’re excited to share Overland with families worldwide. In order to give yourself the best chance of getting into your first-choice trip, though, you should submit an application as soon as possible!
We’re also looking forward to meeting families over Zoom in January, as we host Zoom Q&A sessions. Our schedule is available on our website. The Zoom Q&As are a wonderful way to learn more about Overland and ask any questions you may have, or just listen in. Parents and children are welcome to join.
Students and leaders on Berkshire Adventure in 2021
In the meantime, if you find yourself daydreaming about warmer weather, crisp mountain air, and the joy of exploring nature, please take a look at our 2022 trips. As always, please don’t hesitate to reach out with any questions–we’re always happy to chat! Over the holidays, email is best: info@overlandsummers.com
Cheers to all of the adventures that lay ahead in 2022!
Looking forward to seeing all of you in 2022!

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