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.

Challenge, Community, & Camaraderie

Discovery & Inspiration

A group shares a meal after a day of hiking

I first came to Overland as a leader of the Summer Writing Program – now renamed Writing & Hiking New England. As I drove to Williamstown, I was incredibly excited – what could be better than combining my love of writing, working with students, and the outdoors in the beautiful Berkshires? But I also had moments of hesitation at Leader Training, surrounded by my peers preparing to lead biking and hiking trips, packing up tents and camp stoves and panniers. Though we were all leading teen adventure programs, I worried that a writing trip would never measure up to exploring the Alps or the Sierras.

But what became clear on the very first day with our students was that the Overland experience applies to every trip, no matter the itinerary or the destination.

Two girls writing together and discussing their work during their writing program this summer
Hard at work on Writing & Hiking New England.

The idea of “challenge” is different to everyone – it depends on their past experience, their personality, their interests, and their fears. In the Summer Writing Program, some students wrote with pleasure and ease – they relished the opportunity to spend the mornings thinking, crafting their ideas, and sharing their work with the group. But they may have had much more difficulty during our afternoon hikes and bike rides, summoning more strength to summit Mount Greylock than to draft an essay. For other students, writing was the core challenge of the trip. It took persistence and grit to craft their work and vulnerability to ask their peers for feedback. Like all Overland trips, challenge is inherent in a writing or language program; whether it’s editing an essay, learning to converse with a shopkeeper in Spanish, embarking on a challenge hike, or just being away from home, the sense of accomplishment that comes from facing an obstacle is what stays with you after the summer ends.

At its core, the Overland experience is about the group – putting the group first, thinking of others, working together, and building lasting friendships. This is no different on a writing or language trip. During my second summer as an Overland leader, I had the pleasure of leading Language & Hiking France. Our group didn’t bond over long days of biking, but through experiencing and embracing a new culture as a unit. We loved French cuisine and held elaborate “pique-niques” nearly every day for lunch, passing around baguettes and waiting for everyone to be served before “cheers.” We challenged each other to speak French outside of class time and to praise effort, not perfection. Like every Overland group, we closed each evening with Dessert Circle. And though our desserts were a bit different than our friends on trips in California or Costa Rica, we all took the time to reflect on the day and celebrate each other.

On afternoons and on the weekends, students explore the natural beauty around them.

What I loved most about leading for Overland was that my writing and language students had the same experience of challenge, community, and camaraderie that they would on any other trip. Overland’s values guide every leader to deliver an unforgettable summer for students, and I’m grateful to have had that opportunity. 

Editor’s Note: Kate gets at the heart of what we strive for at Overland: teen adventure programs that offer a wide variety of locations, lengths, activities, and challenges while still providing the same carefully-crafted group experience. Search for your next trip here!

Filed Under: Teen Summer Adventures / Teen Adventure Programs / Writing and Language Trips

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