Home Trips Introductory Berkshire Adventure

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?

Duration

1 week

Trip Fee

$1,695

Berkshire Adventure is open to students finishing grades 4-5 in June 2023. We plan to have one group at each departure date, and groups typically have one grade represented or a mix of two grades.

Grade

4-5

Level

2023 Dates

Big Smiles & New Challenges

Caring, Supportive Leaders

A rafting adventure on the Deerfield river

Fun on the Deerfield River

A group of friends on a summer adventure

Fun & Friendship on Mt. Greylock Summit

Teen Summer Introductory Adventure Berkshire Adventure

Biking on Ashuwillticook Rail Trail

Need to Know

Included in Trip Fee

Meals
Group gear
Accommodations
Activities
Bicycle Rental
Albany International Airport shuttle

Not Included in Trip Fee

Personal gear and clothing
(see what to pack)
Airfare to and from the trip start and end
Travel protection (recommended;
learn more about the benefits)

Itinerary

Fun, friends & adventure: the best week of your summer.

Day 1: Trip Start

The trip begins on Sunday in Williamstown, Massachusetts. During our first afternoon together, we’ll focus on getting to know one another through games and a short, beautiful hike.

Days 2 & 3: Exploring the Berkshires

On our first full day, we’ll hike in the rolling hills just north of Williamstown. We will hike up a gradual peak with views of Mount Greylock and the Taconic Crest, which divides Massachusetts and New York. On one of our days, we’ll hop on Overland’s bikes and ride the Ashuwillticook Rail Trail.

Days 4 & 5: Hike Mount Greylock & Raft the Deerfield River

As we near the end of our trip, we’ll climb Mount Greylock, Massachusetts’s highest peak at 3,491 feet. We’ll carry layers, lunch, and snacks in our day packs, working together as we hike to the gorgeous summit. At the top, we’ll celebrate with a group photo and spectacular views of New York, Vermont, New Hampshire, and Massachusetts. To finish our week of exploration, we’ll spend a day rafting the Deerfield River with professional guides. The Zoar Gap, a spectacular section of the Deerfield River, is a great balance of fun rapids (class II and III) and calmer water. On our last night together, we’ll celebrate all that we’ve accomplished, all the friends we’ve made, and all of the fun we’ve had!

Day 6: Trip End

The trip ends on Friday morning in Williamstown with hugs and goodbyes!

Accommodations

5 nights of front country camping. Campground facilities will vary and may include flush toilets, hot water, showers, and laundry.

Itinerary may vary by group and is subject to change.

Testimonials

"I want to thank my leaders and the kids in the 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 much 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.

Illinois

What to Pack

Download PDF

Questions about what to pack? Email your trip planner, Nate Greason.

Luggage

Medium-Sized Duffel Bag or Backpack

3,000-5,000 cubic inch (50-80 liters) duffel bag or backpack.
Day Pack

Basic two-shoulder backpack large enough to hold your lunch, two water bottles, snacks, extra layers, and rain jacket. Use your day pack as a carry-on for your flight and for daily activities or hikes. A standard school backpack is usually fine (no satchels or shoulder bags), as long as it is comfortable to wear.

Clothing

Navy Overland T-Shirt (1)

We will send every student an Overland T-shirt prior to the trip. Please wear this T-shirt to trip start.
Synthetic T-Shirt (3)
Lightweight Long-Sleeve T-Shirt (1)
Synthetic Shorts (3)
Fleece Pants (1)

Please do not bring cotton sweatpants (they are heavy and bulky and will not keep you warm if wet).
Synthetic Hiking Pants (optional)

Lightweight and quick dry material. Non-cotton warmup style pants are acceptable.
Underwear (6)
Athletic Socks (4)
Swimsuit (1)
Hat with Visor (1)
Winter Hat (optional)
Pajamas (optional)

Students sometimes prefer to sleep in shorts and a T-shirt instead of pajamas.

Outer Layers

Fleece Jacket or Pullover (1)
Lightweight Synthetic or Down Jacket (1)
Raincoat (1)

Waterproof material (e.g., Gore-Tex, or similar) is required. Your jacket should be large enough to allow layers underneath. Ponchos are not acceptable.

General Gear

Sleeping Bag

Any type of sleeping bag is acceptable.
Flashlight or Headlamp
Bowl, Mug & Utensils

6" to 8" plastic dish or bowl with top, insulated plastic mug, spoon, fork, and knife. These don't need to be special camping utensils (a Tupperware dish and regular utensils are fine).
1-Liter Water Bottle

Bike Gear

Bike Helmet

If you are flying to trip start, carry your helmet on the plane with you.

Footwear

Sneakers

Comfortable shoes with good traction and stability, suitable for walking on varied and rocky terrain.
Water Shoes

Closed-toed sport sandals, water shoes or old sneakers to wear on the water. Sandals must have a heel strap for activities such as kayaking, rafting, or canoeing (flip flops and Crocs are not acceptable).

Miscellaneous

Synthetic Camping Towel

A medium-size synthetic camping towel (synthetic camping towels dry much faster than regular towels).
Travel Size Toiletries
Sunglasses
Sunscreen (SPF 15+) & Chapstick (with SPF protection)
Pillow (optional)

Compact, travel-size pillow recommended.
Camera, Charger & Extra Batteries (optional)

A digital or disposable camera.
Personal Journal or Book (optional)

Important Documents

Health Insurance Card

Please bring an original or copy of your health insurance card.
Photo Identification

If you are not flying: Overland does not require photo identification. If you are flying within the U.S.: The TSA website has two relevant pieces of information. (1) “TSA does not require children under 18 to provide identification when traveling with a companion within the United States.” This language indicates that TSA staff can insist that an under-18 year old who does not have a companion (we interpret this as a companion who is 18 or over traveling with them—not just checking them in) must have TSA-compliant identification. Our experience is that this requirement is inconsistently enforced but, since it might be enforced, we recommend that all Overland students who are flying to/from their trip have TSA-compliant identification. (2) “Contact the airline for questions regarding specific ID requirements for travelers under 18.” This is always smart to do as airline policies vary widely and change frequently.

Spending Money

Spending Money & Miscellaneous Expenses

Each student should bring a debit card, an ATM card, or a prepaid Visa card to cover spending money and miscellaneous expenses. Spending Money: While all meals and activities are included in the trip fee, we recommend $25/week for spending money (for example: for souvenirs or an occasional drink or snack beyond what is provided to the group as a whole). Miscellaneous Expenses: Most Overland students will incur some expenses while traveling (for example: an equipment repair or baggage fees at trip end). Please add $100 to the debit/ATM/Visa card (in addition to spending money), to cover these expenses.

Things to Know

Please do not bring your smartphone (or any other electronics).

Please visit the FAQ tab for more information on our cell phone and electronics policy.
Do not bring any type of knife or multi-tool (such as a Swiss Army knife or Leatherman tool).
If you are flying to your trip, carry your sleeping bag with you in case your checked luggage fails to arrive on time.
Sleeping pads will be provided by Overland.
There are no reimbursements for lost, damaged or stolen items.
Please schedule expensive items—phones, cameras, etc.—on your homeowners insurance policy.

If you’re looking to purchase a backpack, fleece layers, etc., for your child, we encourage you to consider borrowing, renting, or purchasing lightly used gear. Especially for children who are still growing, using pre-owned gear can reduce both waste and cost.

Please note that some items wear out over time, and are best to purchase new (for example, a GORE-TEX raincoat). As with any gear, please make sure the items fit your child well. If you have any questions, please give us a call (413-458-9672) or email us (info@overlandsummers.com).

Here are a few reliable places where you can purchase used items:

FAQs

How challenging are Overland's Introductory trips?

These trips feature a wide range of fun outdoor activities–including hiking, biking, basic rock climbing, introductory rafting, and flat-water canoeing.

Trips vary by length (one week or two weeks) and location. As on every Overland trip, our leaders provide a warm, welcoming, and fun environment in which everyone is included and supported. Introductory trips are the perfect place to discover the outdoors, try a new activity, and make new friends.

We’re always happy to tell you a bit more about our introductory trips– just email us: info@overlandsummers.com.
Does my child need to have previous experience?

While no previous experience is required, we have high expectations of our students.

We expect your child –with your help– to select a trip that is appropriate for their interests and abilities. You should spend some time familiarizing yourself with the details of the specific trip and help your child understand what to expect.

We also expect our students to prepare ahead of time: to review the packing list, gather clothing and gear, and complete whatever training the trip requires (for recommended training please see the Before You Go tab).

Once the trip begins, your child should be ready –and excited– to contribute to a wholesome and enthusiastic group in which each member feels welcomed and valued.
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:
1. The applicant is placed on the applied-for trip if the applicant otherwise qualifies.
2. We offer a different trip if the applicant otherwise qualifies.
3. 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!).
My child doesn't have experience being away from bathroom facilities. Will Overland's leaders teach and support the group?

Yes. We want each of our students to feel completely supported.

Every one of our trips will spend some of their time in areas with access to bathroom facilities, many of which include flush toilets, running water, and trash receptacles. Our youngest students, and those participating in service and language trips, will spend most of their time in settings like these.

All of our hiking trips will spend time away from areas with bathroom facilities. In preparation for a day hike away from facilities, or for a longer backpacking section, our leaders will teach the group about backcountry bathroom practices. In most cases, this will include digging a cat hole (a shallow six-inch hole) in a private location away from water sources. Leaders will also provide every group member a small bag to pack out toilet paper (and other paper products, e.g., pads and tampons).

Our leaders will also make sure that group members are supported with menstruation information, needs, and supplies (i.e., pads, tampons). We recommend sending your child with a supply of these items. If your child needs additional pads or tampons, the leaders can provide them.
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 Overland, please do not send an expensive smartphone. Instead, an inexpensive prepaid cell phone will do. All phones will be collected on arrival and returned at departure. While we will take reasonable steps to prevent damage, theft, or loss, 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.
Can I send mail to my child during a trip?

Getting a letter, card, or postcard while on an Overland trip is always exciting.

Please keep in mind that sending mail to your child on an Overland trip is different than sending mail to a traditional camp because your child will be on the move. Our experience has been that mail often does not arrive on time, and sometimes even when it does, post offices, campgrounds, and other mail stops do not reliably deliver mail to our groups.

For these reasons:

1. Please do not send anything valuable – please send letters, cards, or postcards only. If mail is late, lost, or misdirected, Overland’s leaders and staff are not able to return to the post office (or other mail stop) to collect it.

2. Please use the US Postal Service first-class mail only; do not use UPS, FedEx, or DHL (many of our mail stops accept US Postal Service mail only).

3. Please do not send overnight letters: many overnighted letters arrive before or after we arrive and are sent back. For this same reason, please do not send mail that requires a signature upon delivery.

4. Please allow one week for delivery to U.S. mail stops.

5. Please allow two weeks for postal delivery to international mail stops.
My child’s birthday is during the trip — can I send a gift?

We recommend that you send a letter, card, or postcard instead and save the gift for when your child returns home at the end of the trip (and, don’t worry; your child’s trip leaders will make sure there is a celebration!).
Can I send my child a care package during the trip?

We recommend letters, cards, or postcards instead of care packages. If, however, you send a care package, bear in mind that many don’t make it to the intended recipient (because we’re moving), and that many aren’t returned to the sender.
Where does this trip start and end?

Your child will fly to and from Albany International Airport (ALB), and we will provide a shuttle to Williamstown, Massachusetts.

If your child is not flying to the start of the trip, drop off and pick up is on the campus of Mount Greylock Regional School in Williamstown, Massachusetts.
What is Overland's Covid-19 policy?

Our full Covid-19 policy can be found here.
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.

For more information, and to access our application, please visit our Apply page.

Before you Go

Hike, bike, and raft in the Berkshires of Massachusetts.

Students going on Berkshire Adventure should prepare for:

Full days of active exploration
Camping and preparing meals outdoors
A fun, supportive, and wholesome Overland experience

We expect you to arrive to your trip fully prepared for all activities.

Preparing for an Overland Experience

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.

Covid-19 Information

This summer, we are asking all of our students

To be vaccinated for Covid-19, and we recommend being up-to-date on available boosters.
To test before their trips. The test can be a clinic-based PCR or rapid antigen test, or a home test. Please note: (a) We will not require families to upload the results of these tests (unless the family has received an exemption or exception to our vaccine requirement); (b) If your child has had (and fully recovered from) Covid-19 within 90 days of their trip start, there is no need to do a pre-trip test.
To mask up when traveling to your trip. In airports and on planes, please mask up. This could help keep you—and everyone in your group—healthy for the duration of your trip.

Overland

Berkshire Adventure