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.

How to Prepare For A Teen Adventure Trip

Teamwork & Leadership

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

As any Overland student knows, preparing for an outdoor adventure trip can be a bit nerve wracking. Whether you’re embarking on Berkshire Adventure for one week or the Alpine Challenge for three weeks, the anticipation of that first day is the same. Will I like the other kids in my group? Will I be able to keep up on our hikes? Even experienced Overland students feel this nervousness — the beauty of Overland is that every trip offers a warm, welcoming environment with new friends, new leaders, and new challenges to discover.

Here are three important ways to prepare for your Overland trip
  1. Read the catalog and the website to understand what your trip will be like.
  2. Get your clothing and gear organized.
  3. Spend some time breaking in your hiking boots (and keeping fit!).

Let’s take these points one at a time:

Read the catalog and the website

This is a simple– and important way– to know what to expect. Once you’ve spent some time with the catalog and on the website, talk to your family about the trip, and together find the answers to any questions you still might have.

Get your clothing and gear organized

Do this well ahead of time. And stick to the list on your trip’s website page (to see the clothing list for one of our most popular summer hiking trips click on this page and scroll down: Rocky Mountain Explorer).

Spend some time breaking in your hiking boots (and keeping fit!)

Well before your trip starts, make sure you have the boots you’re going to use on the trip. Wear these boots on long walks (at least thirty minutes), and wear them as much as you can when you’re around the house, at school, or outside exploring. All of this activity will help you stay fit, and that’s important too!

While you’re getting ready, so are your Overland leaders

What Overland students might not realize as they pack and prep, is that their leaders are getting ready for the trip, too. Just like you, they’re feeling anticipation, eagerness, and excitement for what the summer has in store.

Your Overland leaders will be ready to welcome you

While students gear up for their trips at home, Overland leaders arrive in Williamstown for ten days of Leader Training. They learn everything there is to know about leading a teen adventure trip the Overland way: how to welcome and support their students, the ins and outs of their trip logistics, and most importantly, how to build a cohesive group and ensure a fun, meaningful summer for every student.

Committed and hardworking, Overland’s care about their students’ experience. Before each trip, leaders spend hours reviewing each student’s name, information, and photo so they’re ready to greet them. They triple check their group gear and their trip itinerary. And with this preparation, they’re ready to start the trip, to explore together, and to see what the summer will bring.

The Ovlerand staff during sitting outside together at sunset during leader training for their summer trips with kids.
Overland’s Leaders at Leader Training
Okay, you’ve done the prep work, now how to manage nerves on the first day of camp?

Being nervous on the arrival day of your Overland trip is perfectly normal. And that’s true whether your trip is in the U.S. like Overland’s Yellowstone Teton Adventure, or really far away, like our Kilimanjaro Expedition.

Here are some tips to manage your nervousness on the first day of camp: (1) Be reassured that everyone feels this way (even the kids– and parents– who appear to be so at ease!); (2) Remember that everyone at Overland cares about you, and wants you to have fun, make friends, and feel a tremendous sense of accomplishment, and (3) Trust your leaders: they’re going to make sure that everyone works together to help you feel at home.

The magic of Overland happens within minutes of your arrival. Names are put to faces. Hugs are exchanged. Frisbees are tossed. The nervousness turns into full-fledged excitement — for both leaders and students. There is beauty in seeing a group come together for the first time, to see them move past anticipation and ease into the experience. Once the trip starts, the adventure can officially begin!

A leader smiling in a circle of 4th and 5th graders while playing a game as they first meet each other before their adventure.
Playing Games at Trip Start
Final Thoughts: After the start of the trip this is how Overland supports homesick students

Homesickness is normal: our homes are places of familiarity and comfort, with established relationships built on love. It’s hard to leave all of that! Here at Overland, we recognize that a summer hiking adventure away from home is both a challenge and an incredible gift. We understand homesickness and provide a warm, loving, and supportive family-like environment on each of our summer adventure camps. For almost forty years, and over the course of providing hiking trips for over forty thousand kids and teens, we have learned that caring leadership, gentle encouragement, and a thoughtfully planned itinerary with activity-filled days is the best way to help each of our students settle into the Overland experience, to make friends, to have fun, and to be proud– so proud!– of all of their accomplishments, both big and small!

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