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.

Writing & Hiking New England

Two weeks of learning and fun.

Improve your writing while exploring the Berkshires.

Writing & Hiking New England offers mornings in small classes with inspiring teachers followed by afternoons—and a weekend—of hiking, rafting, and exploring.

Supportive trip mates, dynamic leaders, and experienced teachers: these are the key components of Overland’s writing programs. As an individual writer, you will explore your voice and improve your skills. The class meets in the morning (when everyone is fresh) and works hard for three hours — a significant, sustained engagement with the coursework.

We can’t write all day, so in the afternoon, it’s time to get outside. And what an outside it is: the Berkshires and Vermont’s Green Mountains are ideal for hikes. Of course, the first hikes are shorter and easier, but working at it every day soon increases everyone’s skills and fitness — yours, too.

On the weekend, it’s time to camp and raft. It’s perfect: after a week of great classwork and fun afternoon hikes, we’ll be ready for a change, for more. So we’ll organize the camping gear, pack up, and head for the hills. After camping and hiking, we’ll raft the Deerfield River.

During the second week, we’ll pull it all together. Not just the writing (developing a portfolio), and not just the hiking (climbing the tallest mountain in Massachusetts), but the whole experience: learning and fun and friends and everything that makes an Overland summer great. We will realize that the strength of the experience is in the relationships — the friendships that make the hard work fun, that keep spirits up on the trail, that fill every day with laughter and smiles.

You’ll head home a better writer. But just as importantly, you’ll head home more fit, with new friends and fond memories. Writing & Hiking New England — an ideal learning environment, certainly, but more than that, much more than that.

Have a question about availability?

Contact Us or call: (413) 458-9672

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Overland offers introductory, hiking, biking, language, writing, service and field studies programs domestically and abroad for students in 4th through 12th grade.