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.

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Hometown: San Francisco, California

Alpine Challenge   •   Summer of 2019

Hi! I'm Katherine, and I'm a junior at San Francisco University High School. Outside of school, some of my favorite activities are backpacking, camping, skiing, and writing. The Alpine Challenge was my second Overland trip (I also did Alaska Expedition in 2018). I loved both the Alaska Expedition and Alpine Challenge, and I got to meet some of my best friends on both trips. In the future, I hope to be an Overland leader or work in the Overland office!

The best way to describe Alpine Challenge is transformational, rewarding, and so beautiful!
The Best Part…

The best parts of the Alpine Challenge were the people I met and the places we explored. The people on my trip were some of the most kind, passionate, funny people I know, and they're some of my best friends to this day. We all grew close very quickly because of the challenging hikes we were doing and because we were all really excited about the places we were exploring together. And, I mean, is there any other way to describe the Swiss Alps other than stunning?

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The Most Unexpected Part…

The most unexpected part of my trip was how good the food was and just how much ground my group covered. Almost every day of the trip, we had access to a grocery store or bakery where we got fresh fruit, veggies, chocolate, and bread which was such a treat. At the beginning of the trip, I decided to keep a journal of our mileage and in the end my group hiked upwards of 220 miles which was so cool. I felt that I could do anything after that!

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My Group…

My group was like a family and still is. I met some of the most funny, kind, motivated people on the Alpine Challenge. Every day, my group-mates all woke up excited to crush the day’s hike and push themselves and each other. On the trickiest climbs, we all looked out for one another and it was amazing how selfless and endlessly kind everyone in my group was. I can't say I've met more optimistic, happy, all-around great people at one time, and I'm so grateful for how close we all got.

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My Leaders…

Harmon and Elena were simply great people. I always felt that I could talk to them if I felt homesick or nervous about a hike and they would patiently listen to me and make me laugh. I also always felt safe when I was with them because they were so calm, collected, and responsible, with a solution to every situation. They were also some of the funniest, coolest people I've met, and I aspire to be like them when I'm older.

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What advice would you give to someone who is thinking about doing this trip?

If you're on the fence about doing Alpine Challenge, do it! As hyperbolic as it sounds, it was one of the highlights of my life, and I promise you won't regret it. If you're someone who's prepping for the trip, make sure you're following the training schedule as much as you can because the hiking on the trip is pretty rigorous and the training makes the transition easier. Happy trails!

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