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.

A Personal Touch

Teamwork & Leadership

Leader learns how to change a flat tire while preparing for his summer biking trip

After six summers as an Overland student and leader, I joined Overland’s Operations team. Operations joins forces with the year-round staff in Williamstown to make sure every summer runs smoothly. In my time with Operations, I managed thousands of pieces of gear, shuttled dozens of leaders to airports, joined countless New England-based trips for hikes and pizza parties, and woke up bright and early for both long days at Leader Training and exciting trip start afternoons. 

Of all the work I did with Operations, however, one thing stands out: bikes. Overland has over 200 bikes that are used by students and leaders all over the country for our summer biking trips. Between trips (and over the winter), these bikes are carefully tuned to ensure that they’re in tip-top shape before they return to service. (These bikes live long, sustainable lives: after three summers with Overland, they’re sold to members of the Overland and Williamstown communities. I have one, as do my mother and sister!) 

A few weeks before Leader Training, the Operations team and I arrived in Williamstown to get to work making sure every bike was set to go for that summer’s students. Although there were hundreds of bikes for us to work on, it was a surprisingly personal process. As we started tuning each bike, we identified which student would ride it and which trip it would eventually go on. Olivia in Nova Scotia, Dan on Cape Cod, Emily in Vermont: as I saw the names and trips, my focus was not only on mechanics and components but also on the teen summer adventures and experiences that those bikes would provide Overland students.

Summer Biking Trip leaders wearing helmets prep their bikes for a day of training

This personal touch is at the core of the Overland preparation process. The admissions team gets to know each and every student as they place them in a carefully crafted group. Leaders learn students’ names and a bit about them before they’ve even arrived at trip start. And those of us on the Operations team have the students in mind as we contribute to the countless hours of preparation that lead up to each student’s arrival. 

Editor’s Note: It is remarkable to see the effort and care put into each piece of preparation for these trips – whether it’s planning out meals, learning student names and hometowns, or making sure a bike rides just right. Operations staff like Owen do an incredible job of facilitating a smooth transition for our leaders and our students, so they can focus on being present with the group. See the summer biking trips Owen mentioned above here.

Filed Under: Teen Summer Adventures / Teen Summer Biking Trips / Operations

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