Berkshire Adventure

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

With a wide range of fun outdoor activities — from hiking and biking to camping and rafting — Berkshire Adventure is a great place to start 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 — this is the kind of experience you are going to want to come back to year after year. A week of adventure 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, 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 we’re focused on building confidence and independence during their time with us.

We’ll begin with easier hikes, building up to our hike of Mount Greylock, the highest point in Massachusetts. The hikes early in the week are designed to give everyone a chance to enjoy being outdoors while developing skills and fitness. We’ll hike as a group and take lots of breaks — for water, for snacks, and for lunch. By the time we take on Greylock, the group is ready and it’s an exciting day with cheers and hugs at the top!

The biking we’ll do is on the car-free Ashuwillticook Rail Trail. Rail trails are ideal for biking on our adventure trips: there are no cars and the trail is essentially flat (and it’s well paved). We’ll bike with helmets on, and with a leader at front and rear of the group. We’ll stop frequently for water, we’ll have snacks mid-way, and we’ll have fun as we go, enjoying a different way to experience the outdoors.

Rafting on the Deerfield is a blast. The Deerfield River, a dam-controlled river, has the kind of rafting that’s ideal for our groups: with professional guides at the helm we’ll enjoy fun rapids — just the right amount of fun for beginners on our exciting day on the water.

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.

Making meals at Overland is a fun 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.

At trip end, we’ll celebrate all we have accomplished on Berkshire Adventure — a great week of camp and the perfect introduction to Overland.

Berkshire Adventure was our very first introductory trip. It’s a great place to start for 4th and 5th graders: a week that’s just adventurous enough with a carefully chosen slate of outdoor activities. This all happens with caring leaders providing excellent supervision to a small group of kids. The activities are fun, and the tone is always warm and welcoming. Berkshire Adventure has always been a great success for us — and it can be for your child, too.

Good Things to Know. The group is always small — no more than 12 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 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 is Overland’s home base with easy (about three hours) access to Boston, Connecticut, New York, and New Jersey… and there are good flight options from around the U.S. on United, American, and Southwest into the Albany, New York, airport (an hour away… and we provide a supervised shuttle both ways).

Have a question about availability?

Contact Us or call: (413) 458-9672