Adventure
Grades 4 - 6

Berkshire
Adventure

A terrific first trip

Berkshire Adventure
is a great place to start

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. 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.

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“I want to thank my leaders and the kids in my group for making this week one of my favorites…

I am already thinking about which trip I want to do next year. Overland is so fun!”

Colette B.

Massachusetts

“Best camp ever!

He came home and said, ‘we should camp on our next vacation.’ I feel like it was life-changing, especially for a city kid!”

Jennifer S.

Parent of Sam | Massachusetts

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Download the Berkshire Adventure Itinerary for
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Planning the journey –
Good Things to know

Group Size
The group is always small — no more than twelve students total.
Leaders
We always have carefully chosen and thoroughly prepared leaders.
Challenge
Age-appropriate challenges, culminating in a hike up Mount Greylock!
Age Range
Groups typically have a mix of two grades (4th & 5th, or 5th & 6th grade).
Travel
Albany International Airport is only an hour away and we provide a free, supervised shuttle both ways.
Meals
Meals are wholesome, nutritious, and varied… and they’re fun group projects.
Activities
Day hikes, one day of biking, and one day of rafting.
Accommodations
The camping is in private campgrounds and state parks that offer full facilities.

your questions, 
answered

With 40 years of experience, we’ve learned what works and what doesn’t when crafting a great outdoor summer experience. Our team is just a phone call or email away.

View more frequently asked questions ›

Have more questions or want to inquire about availability?
Contact Us or call: (413) 458-9672

How challenging is this trip? What do I need to prepare for?

Students going on Berkshire Adventure should prepare for full days of active exploration, camping and preparing meals outdoors, and a fun, supportive, and wholesome Overland experience. The group will average 4 miles on trail, spend 1 day cycling on a bike path, and enjoy 1 day of rafting .

We expect you to arrive to your trip fully prepared for all activities. Each of our introductory trips is a carefully crafted experience with activities that are finely-tuned for this age group. The day hikes are chosen with care so that our students can enjoy hiking while developing skills and fitness. The group is ably led by caring Overland leaders who make sure that each student has water, snacks and lunch, a hat, sunscreen, and a raincoat before the group sets out for the day. Once on the trail, there are stories and songs, and once at the destination — a viewpoint or mountaintop — there are cheers and hugs.

To be ready for an Overland introductory trip, each of our students should stay active and fit during the school year, and once the trip starts, they should be eager to try new things and make new friends.

What kind of gear do I need to bring?

Students are responsible for bringing their own personal gear, including weather appropriate clothing, sturdy shoes & boots for hiking, and a suitable daypack and/or backpack. Clothing should include moisture-wicking base layers, mid-layers for warmth, and windproof/waterproof outer layers. Overland will provide any needed group gear, including tents, food, pots and pans, etc.

What do I need to know about traveling to/from this trip?

You will need to arrange transportation for your child at trip start and trip end. 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). We will provide more specific travel information once we have placed your child on a trip.

What are meals like at Overland? Can Overland accommodate allergies and intolerances?

Meals at Overland

Good food (and plenty of it!), excellent nutrition, and fun are the goals of Overland’s meals. Each group buys, prepares, and eats all of its meals together. Our students, with their leaders’ supervision, prepare all meals. A typical breakfast has cereal, milk, juice, and fruit; most lunches are sandwiches (or wraps) with a variety of fillings, plus chips, and fruit; dinners reflect easily prepared group meals like pasta, burritos, and stir-frys (all of which will typically have a selection of sauces and fillings). At Overland, meals are a group experience, an important way to foster connection with and consideration for other group members.

Allergies Intolerances

We recognize there are many young people with food allergies or intolerances. We welcome these young people’s interest in joining us, and we ask parents of a prospective Overland student with an allergy/intolerance to please consider the following important information.

Most meals at Overland are prepared in basic kitchens (or outdoors), and groceries are typically purchased from small stores with limited choices. As a result, meals are prepared and served in what may be allergen-contaminated environments, and on many trips allergen-free/gluten-free foods are not readily available. While we cannot guarantee allergen-free meal settings, we will do what is reasonable to provide allergen-free/gluten-free foods on those trips where available.

In all things, our top priority is to help maintain all students’ well-being; to this end, all Overland leaders are trained to recognize and respond to allergic reactions, including administering antihistamines and epinephrine (both are carried in every trip’s first aid kit); leaders carry cell phones, and in some cases, satellite phones, so that should the need arise, emergency personnel can be contacted and their services requested. It is important for all prospective parents to understand that many groups travel in remote areas where emergency services may not be easily or readily accessible.

Our Admissions Process is Collaborative

During our admissions process, we will review all submitted Allergy Questionnaires to understand the applicant’s allergy/intolerance. We will then consider whether or not the applicant’s allergy/intolerance may be reasonably accommodated. If our admissions team has any concerns, they will contact the parent. In this conversation, we will seek to learn more about the allergy/intolerance, and we will discuss the available grocery stores, emergency services, and medical facilities on the applied-for trip. These conversations generally have one of three outcomes:

  • The applicant is placed on the applied-for trip if the applicant otherwise qualifies.
  • We offer a different trip if the applicant otherwise qualifies.
  • We recommend waiting a year and re-applying.

Managing Food Allergies/Intolerances is a Partnership

Our commitment is to the health and well-being of each of our campers. Our goal is to partner with parents and campers—a partnership in which:

  • We clearly describe our trips and policies;
  • Parents clearly describe their child’s allergies or intolerances and their child’s maturity level and capability to self-manage their allergy or intolerance.
  • We work together with parents in a collaborative and interactive process to determine if there are reasonable accommodations that can be made so that otherwise qualified applicants can participate in our trips.
  • Students on an Overland trip take an active role in managing their allergies, including reading food labels as needed, eating only those foods with known ingredients, and seeking a leader if a reaction is suspected.

Meals: Vegetarians Specialized Diets

Every summer there are many vegetarians who join our groups and who enjoy meat-free meals. We are happy to welcome these students as long as they understand they will share in the group’s meals but will simply have the meat portion withheld. For example: sandwiches at lunch with hummus, lettuce, tomato, and cheese (while the rest of the group has sandwiches with sliced turkey or ham); pasta at dinner with a tomato sauce (while the rest of the group has pasta with a meat sauce). We sometimes have requests from applicants with specialized diets—vegans, for example—to provide separate, specialized meals. As much as we might like to accommodate these applicants, the limitations of our kitchens, the size of available grocery stores, and the importance of group meals make it impractical to provide separate, specialized meals.

How often will there be access to showers and laundry? Will my child have to bring quarters and detergent for laundry?

Staying clean and comfortable is important at Overland!

Most trips have frequent access to hot showers. This ranges from nearly every night on some of our Introductory, Service, and Language trips, to every couple of days on many hiking trips, to longer stretches–three to five days, sometimes a little longer–on some of our more challenging trips. The goal on every trip, however, is to take showers when they are available!

In general, on every trip we do laundry once a week– this is typically in a laundromat with funds and detergent provided by Overland (and it’s usually a lot of fun!).

What are Overland’s policies on phones, electronics, and communication?

Phones

To maximize independence and self-reliance, we do not permit phone calls, emails, or text messages to or from our campers. Your child will call home on arrival and departure with our phones and assistance, and in the case of an emergency. If your child brings a phone for use while en route to their trip, please note that all phones will be collected on arrival and returned at departure. While we will take reasonable steps to prevent damage, theft, or loss to phones, we take no responsibility for phones, and we will not make any reimbursements for lost, damaged, or stolen phones.

 Electronics

Cameras are welcome but please do not bring any other electronics (e.g., iPods, iPads, Kindles or other readers, GPS or similar devices). All electronics (except cameras) will be mailed home on arrival (at your risk and expense).

Communication: We’ll Be In Touch With You If Needed

Our leaders in the field check in with our office regularly; they carry cell phones (and in some cases satellite phones). Anytime a camper is treated for an injury or illness by a doctor or other medical personnel, parents are notified by our office. A director will call the parents to explain the nature of the injury or illness, the sequence of events leading up to the injury, and/or the steps leading to the treatment. Parents are typically able to speak with the medical personnel, with the leaders, and with their child.

Please tell me about safety at Overland.

Safety and risk management are at the forefront of our decision-making–from trip planning to leader training to supporting our groups in the field.

We cannot guarantee absolute safety–no program can. All recreational activities include inherent risks. Therefore, we strive to manage the risks that we can, knowing we cannot eliminate them.

We work hard to recruit, train, and support our trip leaders so they can create the kind of trips that have made us successful since the 1980s.

Please click here to read more about our approach to risk management and our accreditation by the American Camp Association.

What is Overland's admissions process?

When we receive your application, if your first choice is available, we will:

  1. email you to thank you for your application,
  2. send you a link to access your Family Portal, and
  3. charge a deposit of $795 to your credit card.

If your first choice is not available, we will email you to discuss options.

What might students learn while on this trip?

Students on Berkshire Adventure will spend time hiking, rafting, and biking, and will be taught a variety of technical, leadership, and interpersonal skills throughout their trip.

Throughout the itinerary, students will learn to set up a tent, pack a daypack independently, and practice the basics of Leave No Trace. Additionally, students will have a chance to be leader of the day, calling out water and snack breaks on trail, and lead an activity or game while at camp. All Overland students will work on the following interpersonal skills: initiating group activities, building conversational skills, conflict resolution, giving and receiving feedback, finding compromises, and modeling leadership. 

The goal is for Overland students to achieve proficiency; even if they aren’t mastering all skills, students will build on their knowledge and further their experience.

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