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.

Berkshire Adventure

Few settings rival the Berkshires as a location for an introductory Overland hiking trip.

With a wide range of fun outdoor activities, Berkshire Adventure is a great introductory hiking trip for our youngest students.

As with every Overland trip, Berkshire Adventure offers a supportive, wholesome setting and caring leaders. Every day, the focus is on having fun and making friends — and getting used to adventuring away from home. A week of hiking and fun in the beautiful Berkshires. Come explore with us!

Nestled in the northwest corner of Massachusetts, the Berkshires offer an inviting landscape of hills and mountains, rivers and lakes. Across the region, small towns dot the countryside, offering a look into a quieter way of life.

On Berkshire Adventure, the activities — hiking, biking on a car-free rail trail, camping, rafting, and playing games — are all carefully calibrated to suit our youngest campers. At every step of the way, Berkshire Adventure offers appropriate challenges in a supportive and nurturing environment with Overland leaders who are attuned to the needs of this age group. For many of the campers on Berkshire Adventure, this is their first time having an experience like this, and their first time hiking, so we’re focused on building confidence and independence.

We’ll begin with easier hikes, building up to our hike of Mount Greylock, the highest point in Massachusetts. The biking we’ll do on the Ashuwillticook Rail Trail is perfect for younger campers: there are no cars, the trail is essentially flat (and well-paved), and we’re always practicing safe riding, with helmets on, and a leader at the front and rear. Finally, rafting on the Deerfield River is the perfect amount of fun to finish up a great trip. With professional guides, we’ll enjoy exciting rapids on a beginner-friendly river. During all of our activities, we make sure to take plenty of time to stop for snacks, water, more snacks, and fun games as a group.

Camping on Berkshire Adventure is fun — and comfortable! We’ll stay in privately-owned campgrounds and state parks. Showers are always available so after a day on the trail, or on the bikes, or on the Deerfield River, we’ll get cleaned up. We’ll practice setting up tents and get used to sleeping in our sleeping bags. After long days of fun, a good night’s rest is just what we need to get ready for the next day.

Making meals is always a group project. At Overland, we have six meals a day: breakfast, morning snack, lunch, afternoon snack, dinner, and dessert. Everyone joins in as we plan, shop for, cook, and clean up after each of our meals, always looking for healthy, fun choices that everyone will enjoy. Leaders provide careful supervision while also allowing campers to start gaining some confidence in their cooking abilities.

At trip end, we’ll celebrate all we have accomplished on Berkshire Adventure — a great week of hiking and camp and the perfect introduction to Overland. Berkshire Adventure was our very first introductory trip, and all these years later we still think it’s the perfect place to start for 4th and 5th graders.

Good Things to Know. The group is always small — no more than twelve students — and we always have carefully chosen and thoroughly prepared leaders. The itinerary is crafted to provide just the right mix of activities — the goal is to have every student love their Overland hiking experience. The camping is in private campgrounds and state parks, all of which offer full facilities, including hot showers. Meals are wholesome, nutritious, and varied… and they’re fun group projects with input from everyone and guidance from the leaders. Getting to and from the trip is a breeze: Williamstown has easy access to Boston, Connecticut, New York, and New Jersey… and there are good flight options from around the U.S. on United, American, Delta, and Southwest into the Albany, New York, airport (an hour away… and we provide a free, supervised shuttle both ways).

Have a question about availability?

Contact Us or call: (413) 458-9672