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.



Hometown: Newton, Massachusetts

Pyrenees Expedition   •   Summer of 2019

Hi! I'm Kendra and I'm currently a first-year at Hamilton College. I'm an intended Government major and I'm on the club Nordic ski team. Pyrenees Expedition was my fourth Overland trip. I'm thrilled to be joining the Overland team in Summer 2021 as part of the support staff!

Pyrenees Expedition: Stunning views, quaint towns, and an amazing adventure.
The Best Part…

The best part of the trip was hiking through cute mountain towns in the Pyrenees. I loved stopping in the villages and looking at the architecture and flower boxes. It was also cool to practice my Spanish skills by buying some snacks in local stores. Additionally, I appreciated that this trip was dedicated to hiking because I loved spending every day on the trail.

The Most Unexpected Part…

The most unexpected part of my trip was when we shared the trail with a herd of cows! We were hiking on a trail when we saw a few cows, but we didn't know it was going to be a whole herd. We stepped off of the trail for a few minutes to let them safely pass.

My Group…

My group worked together really well. Everyone was supportive and encouraging if any group member was having a tough day. I loved cooking together and sharing meals as a group after a long day of hiking. Cheers to a great group!

My Leaders…

Kelsey and Sam were awesome leaders! They were so kind, organized, and trustworthy. Kelsey and Sam tied the group together and made sure all our needs were met. I could always count on them for a good conversation while on the trail. I know everyone in the group looked up to them, and they definitely inspired me to apply to lead for Overland.


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

Be prepared for breathtaking views of mountains, lakes, and grassy fields. Days on the trail are beautiful and rewarding, but they come with their challenges. If you follow your training schedule, you will be well prepared for the challenges you may face. Definitely bring a camera to snap some photos and a hat to keep the sun off your face!

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