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: Houston, Texas

Canadian Rockies & Montana   •   Summer of 2018

I am a freshman Sustainability Studies and Business double major at the University of Texas at Austin. I am particularly interested in Corporate Sustainability and environmental racism. I love the outdoors, especially when it involves backpacking and cycling. My hobbies include procrastibaking, board games, and searching for cheap eats in Austin. Canadian Rockies & Montana was my seventh (and final) Overland trip! I will be on Overland support staff in Summer 2021. I have been talking about leading for Overland since my first trip, Mountains & Sea Adventure in 2012, so I am incredibly excited for the summer!

The Best Part…

Besides my amazing group, the best part of my trip was the scenery. The Gatorade blue waters of the Canadian Rockies are unrivaled. We saw black bears (from a very safe distance) nestled into bushes as we climbed the mountains, as well. The Canadian Rockies vie for the spot as my favorite mountain range that I have biked.

The Most Unexpected Part…

There was one long-mileage day which was predominantly rolling hills on our way to Waterton, Canada. We rolled through the entrance of Waterton which felt like any other National Park. But, Waterton was a hidden gem. Three miles beyond the gates, a castle-like hotel popped up against the gorgeous backdrop of the Rockies, and not far past that was the charming town of Waterton. It was the best surprise and our buffer day in Waterton was easily my favorite day of the trip.

My Group…

My group was supportive, goofy, and adventurous. We especially loved to explore. In Banff, we went on an impromptu 3-mile hike.

My Leaders…

Sam and Jeff were amazing leaders. Though the trip was only two weeks long, they created a loving, supportive environment with ease. They were also knowledgeable, encouraging, and light-hearted.


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

If you are new to Overland and looking for a challenge, CRM is a really special trip. Two weeks is a great trip length to take in the beauty of the Canadian Rockies, make lasting friendships, and challenge yourself physically. I believe that you can’t go wrong with any Overland trip, but I think CRM is an excellent trip if you are looking to briefly disconnect from technology and explore a more remote landscape by bike. Keep up with your training because the Canadian Rockies are not a simple feat. Finally, once you are on the trip, keep your head up because you don’t want to let the beauty pass you by!

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I am a sophomore at Middlebury College studying International Politics & Economics and Food Studies. In my free time, I...