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

Available

This departure of this trip has good availability. Apply as soon as possible since availability changes quickly.

Limited

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.

Call

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.

Questions?

Call (413.458.9672) or email (info@overlandsummers.com). We look forward to hearing from you.

Bikers in the Rockies during a bike trip

One of the most challenging things I’ve ever done was on an Overland trip. On Canadian Rockies & Montana in 2016, I biked over 100 miles on a century day in northern Montana.

If you’re reading this as someone who has also completed a century, you know what it involves: an early morning, a too-hot afternoon, moments of frustration and of relief (but also “did I really just do that?” accomplishment) upon completion. On a teen adventure trip, it also involves the company and support of eleven other students and two incredible leaders.

View of the mountains and a valley of the Canadian Rockies with a river
Inspiring View of the Canadian Rockies

If you haven’t completed a century day, you may have doubts in your ability to do so. I sure did. I remember lying awake in my tent, not able to fall asleep with nerves and doubts. Would it be as hard as I imagined? Would I be too slow and hold the group up? Would I even make it all the way?

The next day, as the miles passed, however, I realized that there were a few factors that I hadn’t considered in my moments of doubt.

First, I was ready. Deep down, I knew that I was ready. As the miles passed — 10, 20, 30 — it became clear that my training and the first week of my Overland trip had left me more than prepared to crush miles and push into the afternoon.

A group pauses to take in the scenery of the Rockies after a long summer day of biking
Canadian Rockies & Montana Dessert Circle

More importantly, however, were the people behind me. At Overland, the group comes first. Yes, this often means putting the group before yourself. But it also means that meaningful relationships — nurtured and strengthened immensely even in short amounts of time — encourage everyone to do their best. They even push you to do things you didn’t know you could do. As I kept pedaling — 40, 60, 80 miles — I knew that the people I had come to rely on (and who, in turn, relied on me) were behind me. I wasn’t going to let them down. They kept me going.

When we arrived to camp, exhausted but excited, the sense of accomplishment that we all shared was palpable. Inexplicably energized, we laughed, hugged, jumped in a lake and shared a meal. As we had relied on each other throughout the ride, we celebrated together, too. My group, many of whom are now fellow Overland leaders, pushed and challenged me so that I always felt supported. That dynamic is the heart of any Overland trip.

Teens pose on a stone ledge with a mountain in the background wearing bright colors after biking
Owen and his 2016 Canadian Rockies & Montana group

Filed Under: Teen Summer Adventures / Teen Summer Bike Trips / Student Experiences


Similar Blog Posts

Three girls carrying their sleeping bags as their summer trip begins.

Trip Start – Build-Up, Preparation, Nervousness, Excitement

Teamwork & Leadership

As any Overland student knows, preparing for your trip can be a bit nerve wracking. Whether you’re embarking on Berkshire...

Teens pose after biking across the country on a teen summer biking trip

The Joy is in the Challenge

Independence & Self-Reliance

Sleeping in a tent for the first time. Summiting Mount Kilimanjaro, the highest peak in Africa. Ordering food at a...

A girl smiles while riding her bike and wearing a helmet in front of a hill covered in pine trees.

There’s Beauty Out There

Discovery & Inspiration

It can be easy to forget how much beauty there is out there. Social media, breaking news, name-calling, and an...

All Blog Posts