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.

The Eyes Up Ride

Discovery & Inspiration

BG e

I started thinking about riding cross-country in January of 2021.

I had been a member of the Overland year-round team since September of 2018, and after two years I had begun to think about my next adventure. This would be the first point in my life when I had a blank canvas to work with. As a child, I’d heard stories about the cross-country bike trip my dad took in 1977. Though I often dreamed of completing the same feat, such a lofty goal felt more like an abstract dream – the kind of thing that felt so out of reach that I never considered it possible for myself. While working at Overland, I became swept up in its incredible cycling community and grew to love spending my weekend biking. I became a stronger cyclist and felt confident completing longer, more challenging rides. 
To train for his ride, Ben took advantage of the gravel roads around Williamstown.
As I contemplated my post-Overland life, the idea of a cross-country ride eventually became a real possibility. Even so, it didn’t feel quite right to be setting out on such an adventure purely for my own experience. I wanted it to have a deeper meaning, to give me purpose, and keep me motivated.
Inspired by the work of Overland’s partner, TextLess Live More, I reached out to Executive Director and former Overland leader Marie McGrath. I floated the idea of biking across the country to raise awareness about the dangers of distracted driving while fundraising for TextLess Live More. Marie responded with excitement, and I knew this was the right path forward. From there, my idea turned into a roughly-drafted bike route from Cape Cod, Massachusetts, to Seattle, Washington. My proposed route would hit three must-see landmarks: Niagara Falls, Kenyon College (my alma mater), and Portland, Oregon (to see my sister). Then came a flurry of ideas for my route, which quickly evolved from 4,300 miles to 10,000 miles. With help and support from family and friends, I created a website, an Instagram account, and established a fundraising campaign
Ben’s trusted bike, packed to the brim, among fall aspen trees in Colorado.
As spring wore on, the missing pieces began falling into place.  I ordered a bike, which my dad then had blessed by a priest; I dialed in my navigation plan, and I made arrangements to see friends I’d long missed during COVID.  I put my planning on pause during the Overland summer, so that I could focus my attention on planning great trips and adventures for our students. 

“I wanted the ride to have a deeper meaning, to give me purpose and keep me motivated.”

By the end of summer, and the conclusion of my time at Overland, I had eight days until the start of my ride. In that time, I moved out of my apartment in Williamstown, stored my belongings in my parents’ house, and packed my bike with everything that I needed for the next three months. I then drove to Providence, Massachusetts with my parents. By then, I had reached my original fundraising goal of $10,000. I was overwhelmed by the tremendous outpouring of support. And, I was ready to start the ride! 
Ben at the very beginning of his journey, with 10,000 miles of riding still ahead.
Life had been stripped down to an essential triad: riding, eating, and spreading awareness for an incredibly important cause. 
Since setting out from Providence on August 21st, I have ridden my bike over 5,200 miles across sixteen states. I’ve met countless wonderful people, their interests varying from simply curious to deeply connected to ending distracted driving. I cannot summarize in a blog post all of the amazing things I have witnessed, the compassionate people that I’ve met, and the experiences I’ve had on my trip thus far. I can say, though, that the United States is a vast and beautiful place, filled with the kindest souls imaginable.
The hundreds of miles of bike paths in the U.S. provide safe alternatives to cycling on roadways.
I have nothing but gratitude for the dozens of people who have helped me, for the folks at TextLess Live More who have supported me, and for the opportunity to be riding for an important cause and sharing TextLess Live More’s mission.
Ben passing through Bend, Oregon on the last leg of his push to reach Seattle.
Currently, I am back home in Connecticut for the holidays – resting, stretching, and working hard to fundraise more. In mid-January, I will pick up where I left off—Raymond, Washington—and head south to San Diego. From there, I will turn hard east toward Jacksonville, Florida. By trip-end, I aim to raise at least $50,000. More than that, though, my goal is to put in the effort—the miles and miles of effort—it will take to end distracted driving.
Please follow along and consider supporting this cause at EyesUpRide.com.

Similar Blog Posts

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

How to Prepare For A Teen Adventure Trip

Teamwork & Leadership

As any Overland student knows, preparing for an outdoor adventure trip can be a bit nerve wracking. Whether you’re embarking...


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 summer hiking trip in Norway takes time off the trail to adventure sea kayak

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