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.

Meet Our Teams

Teamwork & Leadership

Group photo of the Overland team that works behind-the-scenes on the teen summer adventure trips and programs

It’s August: summer is winding down, nights are getting cooler, and everyone is squeezing in just one more– one more family vacation, one more s’mores night, one more long and lazy pool day before school starts up again. For our families, Overland is in the rearview mirror: trips are done, memories made, new friends still texting and calling, but now from their hometowns, planning reunions from across the country.

For many of our families, it feels like Overland exists only in the leadup to the summer. There’s a couple months of paperwork and forms, of planning and organizing, and then that brief week (or two, or three, or six!) where the kids are off on their adventures.

For us, however, Overland is just as present in the fall, winter, and spring as it is in the summer. Our full-time staff lives in beautiful Williamstown, Massachusetts, tucked into the Berkshires and just on the border of southern Vermont and eastern New York, where we spend weekends on bike rides or hikes, exploring apple orchards in the fall or skiing through the spring.

Our weeks we spend planning ahead; we have been planning for summer 2020 since spring 2019. Whether we are answering calls from kids who want to know “just how cool the wildlife is,” interviewing college students across the country, or working with an outfitter to create the perfect day of kayaking on Lake Tahoe, we throw our whole selves into creating the best possible Overland summer. And we have fun doing it, too.

Below, read more about our three different teams in the office. We’re excited for you to get to know a little more about us!


Our Admissions team standing and smiling from an office.
Admissions Team (L to R): Harry, Sara, Anya, Laura, Ben, and Brenda (Not Pictured: Emily, Lauren, and Julia)

What good is a campsite if all the other tents are empty? What’s the point of a rafting trip if no one is paddling alongside you? Why learn a new language if you can’t practice with a partner?

Whether imagining a group of 4th and 5th graders making their way up Mt. Greylock, or a band of high schoolers pedaling their way across the country, we in Admissions know that the heart of every Overland teen adventure trip is the same: the group. No matter how distinct each trip’s itinerary may be, they all share this one, common focus. Because while, of course, hiking through the Alps or kayaking on Lake Tahoe can be formative and impactful experiences in and of themselves, what truly makes them special are the people you share them with.

In Admissions, we have the pleasure and the privilege to spend the entire year carefully forming every group, thoughtfully constructing them one student at a time. We know that group dynamics are the key to every trip’s success, and it is this aspect of Overland, not the hiking or the biking or the landscapes, that has kept Overland running for 36 years. The interpersonal nature of Overland has always been, and always will be, our first priority.

Campers stop for lunch next to a river during a teen adventure program this summer
A group stops for lunch and games on a day of hiking.

To make sure that every group is in the best position possible to develop and foster fun and organic group dynamics, we take a careful look at things like hometowns, schools, gender ratios, grade levels, and past Overland experiences when arranging each group. This keeps the experience of every student, no matter their background, consistent: you will be joining a diverse group with the common goals of coming together, accomplishing a challenge, and learning from one another. We also limit the number of friend pairs in each group so that no one ever feels excluded or on the periphery of a pre-formed group of friends. Wholesome, inclusive, and supportive– that’s our goal for every group, each and every summer.

We love this work because all of us have either led Overland trips or have sent our kids on them, so we understand first-hand just how important this is. We work as a team towards one shared goal: making this summer the best it can be for every Overland student. This focus bleeds into everything else we do here at Overland, from hiring excellent leaders who will be the ones steering those group dynamics, to the folks who plan every activity the group will partake in and the gear they’ll need to do it. And when all these details come together— every interview, every tent pole, every admissions form— the end results speak for themselves. Over two thousand kids traveling the world, making new friends, learning from their peers, and growing into kind and responsible young adults. It’s what we do here, and we can’t imagine doing anything else.

Leader Hiring

Leader Hiring Team smiling and laughing while posing in an office
Leader Hiring Team (L to R): Conor, Maddie, and Sam (Not Pictured: Jack)

On the year round Overland team, everyone is passionate about something. For our Admissions team, it’s forming carefully-crafted, well-balanced groups. For our Trip Planners, it’s designing unique trips in beautiful locations with age-appropriate challenges. And in Leader Hiring, we’re passionate about people. Specifically, finding fantastic leaders to lead our Overland students on unforgettable summer adventures.

Leader Hiring is all about people and puzzles. We’re looking for the best people with the right skills and experiences to lead each teen adventure trip. We’re looking for people with tangible skills— backcountry experience if you’ll be leading in Alaska, French fluency if you’ll be leading in France. But more than that, we’re looking for people with intangible skills— people who, first and foremost, love working with kids. We look for people who are already leaders in their communities and on college campuses, so that making the transition to leadership at Overland is natural. We understand that taking care of the well-being of twelve young people is a huge responsibility—and it’s one that we take seriously. Hiring high-achieving, bright, outgoing leaders with impeccable judgement—people that we’ve come to know and trust through our extensive hiring process—is one way we mitigate risk and ensure a safe and healthy summer for all of our Overland students. 

Returning Leader Talks to the group during summer training to lead teen adventures
Talks given by returning leaders help new leaders learn the Overland culture

Leader Hiring hits the ground running in early fall by engaging with our returning leaders. We take a close look at performance reviews, co-leader, student, and parent feedback before making offers to our returning leaders. We put a lot of effort into retaining our leaders because these people come to know and understand Overland the best. Returning leaders make fantastic role models and mentors for our new leaders during leader training and in future summers. Each summer, we have approximately ninety returning leaders and one hundred ten new leaders on staff.

Next, we turn our efforts towards recruitment at the top colleges and universities across the country. In 2019 alone, we visited fifty campuses, connecting with potential leaders and hosting information sessions to spread the word about Overland. We take great care to meet every applicant who makes it to the finalist stage in our hiring process. We revisit many of these same schools each spring to do follow-up interviews and eventually, make our hiring decisions by the end of March.

Two leaders and a middle school-aged child smile from a view point after a hike on their summer trip
We look for leaders who are fun and charismatic, like Jackie and Wilson

Leading for Overland is enormously rewarding. At the end of each summer, the feedback we receive from many of our leaders is that it was the most challenging, yet most fulfilling, experience of their lives. A summer with Overland—the personal growth, the relationships that form, and lessons that come along with it—sticks with leaders beyond a single summer. For our leaders, working with kind, wholesome groups of kids in the outdoors is their dream job. It is an honor and a privilege to welcome these leaders into the Overland community!

Trip Planning & Risk Management

Trip Planning and Risk Management team poses in Overland's office, where they plan teen adventure trip programs
TPRM Team (L to R): Quinn, Will, Meg, Ben, Thomas, and Matt (Not Pictured: Sarah)

In our office, trip planners wear many hats.  From the moment we return to the office in September until the final student departs in August, our goal is to create the best possible experience for our students and our leaders. For all of our trips, the Overland mission is at the heart and core, regardless of the trip type or structure. And from September through June, the Trip Planning and Risk Management team’s primary focus is planning our trips, focusing on the most minute details that make a trip experience excellent.

While the weather is still warm here in Williamstown and our students head back to school, we exhale after a high-energy summer and reflect on what worked and what we can improve for next year. We feel this shift in energy across the office, resetting our minds to the next summer. For the first few weeks of September, we work through the great feedback we receive from our leaders, parents, and students. We garner valuable insight into each trip’s logistics and general structure, which directly influences changes and improvements we make to our trips in the fall– whether it’s reserving the campsite with the nicest fire ring or reworking a challenge hike. We also perform a review of risk management. These details allow us to build our itineraries for the upcoming summer. We contact our outfitters, reserve dates, and plan out accommodations for our trips.

As the weather turns colder, we begin to share exciting new trips and improvements to families. We have the opportunity to talk about our trips over the phone with eager parents who are mapping out their child’s summer, create literature for our website with clear descriptions and trip overviews, and select imagery and details for our beautiful print materials. The smallest detail matters: a description of a day of rafting can be the factor that helps a nervous kid get excited about his first time away from home. All of these tasks enable us to put into action our love for the craft of building a trip. 

Rafting down a glacial river is cool on an Overland teen adventure program
We work with outfitters to carefully craft age-appropriate challenges for our trips

Throughout the year, our hard work and passion for planning Overland’s trips heads out on the road. We spend the coldest months of the year gathering permits and campground reservations and heading out to college campuses and Overland family homes, where we spread the love each of us has for the experiences we create and of which we are a part. During these visits, we are reminded of the warmer months that grow ever closer and start to shift our focus to finalizing trip details and prepare for our leaders’ arrival.

Our busiest months are those directly leading up to the summer. As trip planners, wrapping up the last-minute details and polishing all materials we prepare for our leaders is like readying gifts for a holiday exchange. We may hand off the trip logistics to the leaders at the start of the summer, but we are as engaged as ever while the trips are running. It is our job to make sure the trips run as smoothly as possible and keep the Overland mission at heart.

One Goal

View of a street and clouds above the Berkshires
The view from our office balcony on a beautiful, warm day this March

Though we work on different teams throughout the year, we are always keeping the same goal in mind: to create the best possible experience for our students this summer.

Whether we’re on the phones talking with prospective parents, meeting with local outfitters, or on the road meeting with our leaders, we are always looking ahead to the next “Best Summer Ever”!

Editor’s Note: We love what we do, and we hope you do too. Our ACA-accredited camps are fun, wholesome, and challenging: exactly what we want out of a summer. Call our office at (413) 458-9672 to start a conversation about your family’s summer, or see what sets each Overland teen adventure trip apart here.

Filed Under: Summer Teen Adventures / Teen Adventure Programs / Teen Adventure Trip

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