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.

5 Ways to Build a Close Team

Teamwork & Leadership

Cycling across the golden gate bridge on a teen summer biking trip

If you leaf through the pages of the Overland catalog, you’ll get inspired to do something epic.  The picture of sea kayaking in a fjord is certainly enough to convince a student or a would-be leader to spend their summer one one of Overland’s teen adventure trips.  The team experience, though, brings people back.

My co-leader and I returned to Williamstown two summers ago after our last Yukon trip of the summer feeling full in our hearts, but not because of all the catalog-worthy adventures we had.  Maybe the opposite, actually—we got rerouted on both of our backpacking sections, once by a curious bear and another time by a raging creek. Not every day went according to plan, but we still had fun— more fun than we ever thought possible. We were buoyed by the closeness of our group: I told my friends that it was “a great summer, and we didn’t exactly follow our itinerary word-for-word.” 

Here are five ways to work towards an unforgettable team experience:

A group of students celebrate after finishing biking across the country on a teen summer biking trip
Our American Challenge group celebrates reaching the Santa Monica Pier

1. Create an atmosphere that invites everybody

Overland’s leaders are trained in the ways of the First Talk—the first-day delivery of the trip’s itinerary and the outlining of goals, rules, and expectations (the GREs, I like to call them) for the entire group.  For a student, this can feel like drinking from a firehose. The First Talk normally happens after a long day of travel, meeting your group, and getting to know one another. You’ll have traveled to your first campground, played icebreaker games, completed your first one-on-one check-in with your leaders, and helped cook your first group meal. There’s a lot to learn on the first day— which is what makes the First Talk so important. Setting guidelines and expectations for the trip early on ensures that the whole group is working towards common goals.

What’s helpful is to empower students to create their GREs and decide their team culture. Allowing your group to talk about the kinds of behaviors they want to encourage on their trip— kindness, positivity, and consideration for others, just to name a few— is a great way to let students take ownership over their own experience. By naming the dynamic they hope to foster, students can help hold each other accountable within the group. And, as a leader, you’re able to remind students that they made a commitment to shared values on a trip.

A group of kids and leaders smiling after hiking to the top of a mountain and pose with their arms in the air
When we work together, there’s nothing we can’t accomplish!

2. Manage group dynamics carefully

One of the best parts about Overland groups is that they are supportive spaces devoid of the cliques and pressures that permeate middle school and high school life. The process starts with our Admissions team, who create each group carefully: they balance hometowns, schools, genders, and past Overland experiences so that each student is bringing a unique perspective and experience to the group. They also limit the number of friends per group, so that the majority of kids are coming alone— without knowing anyone else.

But the process of creating a fantastic, supportive group doesn’t stop there. Overland’s leaders are constantly checking in on the group dynamic, making sure that students are holding themselves to the high standards we have for our trips. As leaders, we always say: “Check in on every student, every day.” Understanding the group as a whole, and the perspective of every student in it, allows leaders to steer the group in the right direction.

Sometimes, this means checking in with a homesick kid to make sure they’re doing alright. Sometimes, this means helping point the group towards an activity that invites more people in—a game of frisbee, maybe, instead of a two-man card game. And sometimes, this means just letting the group be the group—recognizing that this is a group of twelve nice kids who want to make this the best experience for every single person.

Teens and leader carry a canoe together as a show of teamwork on their summer trip in Maine
Teamwork makes canoeing in Norton Pond a breeze

3. Step into challenges as a team

Challenge doesn’t need to have a number attached to it—even the “easiest” Overland trips offer challenge and new experiences.  Apprehension should be normalized, too, and can even be talked about in the open. Sharing and acknowledging the anxieties of doing something challenging can build closeness and a shared sense of purpose.

We have a tradition at Overland called dessert circle. Every night, we sit down as a group. Then, as we share dessert, each one of us gets a turn to say the high of our day, the low of our day, and give a thanks to someone we want to recognize that day.

Talking about the lows of our day may feel like the worst part of that tradition: why linger on what was bad? But the low during dessert circle is important. It’s a moment for everyone to talk about what challenged them, for everyone to recognize that the strongest hiker might struggle with preparing food for dinner, that the most outgoing student may have moments of doubt, and even leaders can be nervous on the first day of the trip. By sharing these challenges, we can face them as a group.

Single file for safety on a teen summer biking trip
A group rides together down the California coast

4. Celebrate group successes, not individual ones

Like an endless mountaintop view, success is sweeter when there’s someone to share it with.  The fastest hiker or the cyclist at the front of the line is no more “successful” than the twelfth student to reach the summit.  There is no better feeling than accomplishing a goal—reaching a beautiful viewpoint, or finishing a long climb—and turning to each other, and cheering for our success as a group. Focusing on collective accomplishments also prompts students to celebrate each other. Everyone gets to feel empowered.

At Overland, we often repeat the mantra “Group Before Self.” This means everything from sharing the last of the breakfast yogurt to sharing in the successes of others. This group-first mentality is what makes our trips fun— it’s about the people you’re with first, and the mountains you climb second.

Also, success doesn’t need to be quantified in physical feats.  The most successful I’ve felt as a leader might be after a particularly vulnerable and close-knit dessert circle.  Sharing is successful. Emotional safety is successful. A warm, gooey brownie scramble is definitely successful.

Teen smiling while holding a kayaking paddle overhead and wearing a helmet and lifejacket before white water kayaking on Yellowstone Teton Explorer
Having fun whitewater kayaking on Yellowstone Teton Explorer

5. Don’t forget to play!

Overland trips are busy.  There will always be more miles to hike or ride, more to write, more people to meet or more to learn.  These trips pack a summer’s worth of activities and experience into the space of two or three weeks.  It’s summertime, and the days are long. Eat ice cream. Play weird games. Maybe bring pool floaties up to an alpine lake (but pack them out, obviously).  Take a little time to detach from the rigors of deadlines—these might be the moments students cherish the most!

Editor’s Note: Matt led Rocky Mountain Explorer in 2014, Appalachian Trail Challenge in 2016, and Yukon Leadership in 2017. His tips for leaders apply to students too: Overland’s teen adventure trips are a chance for kids to get outside, have fun, and take ownership over their experience. Read more about Overland’s values here, and explore some of our teen adventure trips for summer 2020 here!

Filed Under: Teen Summer Adventures / Teen Adventure Trips / Summer Hiking Trips / Tips for Leaders

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