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.

Trip Start – Build-Up, Preparation, Nervousness, Excitement

Teamwork & Leadership

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

As any Overland student knows, preparing for your trip can be a bit nerve wracking. Whether you’re embarking on Berkshire Adventure for one week or American Challenge for six weeks, the anticipation of that first day of trip start is the same. Will I like the other people in my group? How will the leaders be? What will I eat? Will I be able to keep up on our hikes or bike rides? Even “experienced” Overland students with a few summers under their belt feel this nervousness — the beauty of Overland is that every trip is different, with new friends, new leaders, and new challenges to discover.

What Overland students might not realize as they pack, prep, and review the Overland website for the millionth time, is that their leaders are a bit nervous, too. It’s the kind of nervousness that is mixed with anticipation, eagerness, and true excitement for what the summer has in store.

Two backpacks and a water bottle with an Overland sticker in a pile.
Leader Backpacks
The Ovlerand staff during sitting outside together at sunset during leader training for their summer trips with kids.
Post-dinner Announcements at Leader Training

While students gear up for their trips at home, Overland leaders arrive in Williamstown for 10 days of Leader Training. They learn everything there is to know about leading a teen adventure trip the Overland way: how to reduce risks, the ins and outs of their trip logistics, how to grocery shop efficiently and effectively for 12 students and 2 leaders, and most importantly, how to build a cohesive group and ensure a fun, meaningful summer for every student. Committed and hardworking, Overland leaders hold a high standard for the quality of their students’ experience — no wonder there’s some nervousness! Before each trip start, 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 even with this preparation, there is still a mystery of the unknown for what the group and the summer will bring.

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
Staff member teachers a leader how to adjust her bike's brakes during training before her biking trip.
Bike Maintenance at Leader Training

The magic of Overland happens within minutes of the first student’s 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 each other. Once the trip starts, the adventure can officially begin.

Filed under: Teen Summer Adventures, Teen Summer Biking Trips, Teen Summer Hiking Trips, Teen Summer Community Service, Teen Summer Language Study Abroad

A group of leaders reading and discussing their work while sitting a picnic table in a field during leader training.
Leader Training Group Work
A group of kids and leaders playing a game to get to know one another of the first day of a summer trip.
Getting to Know the Group at Trip Start

Filed Under: Teen Summer Adventures / Teen Adventure Camps / Trip Start

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