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).
Big Smiles & New Challenges
Caring, Supportive Leaders
Fun on the Deerfield River
Fun & Friendship on Mt. Greylock Summit
Biking on Ashuwillticook Rail Trail
Need to Know
Fun, friends & adventure: the best week of your summer.
Day 1: Trip Start
The trip begins 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 2-4: 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 Tuesday, we’ll hop on our bikes and ride the Ashuwillticook Rail Trail. Between activities, we’ll enjoy the area, swim in a local swimming hole and play group games. On Wednesday, we’ll learn about the land and natural history of the area on a hike guided by the Williamstown Rural Lands Foundation.
Days 4 & 5: Hike Mount Greylock
Next, we’ll start our two-day ascent up Mount Greylock, Massachusetts’ highest peak at 3,491 feet. We’ll carry layers, lunch, and snacks in our day packs, and Overland staff will meet us at our campground (halfway up the mountain) with our remaining gear for the night (sleeping bags, tents, cooking gear and food). The next morning, we’ll continue hiking to the summit of Mount Greylock. At the top, we’ll celebrate our accomplishment with a group photo and spectacular views of New York, Vermont, New Hampshire, and Massachusetts.
Days 6 & 7: Raft the Deerfield & Trip End
To finish our week of fun and exploration in the Berkshires, we’ll raft 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 our accomplishments and new friends with dinner on the town.
5 nights of frontcountry camping. Campground facilities will vary and may include flush toilets, hot water, showers, and laundry.
1 night of primitive camping while hiking Mount Greylock. We will have access to a composting toilet.Itinerary may vary by group and is subject to change.
"Berkshire Adventure was the best week of my life! "
Eli Van der Ryn
"An amazing first sleep away camp experience! Carson is already talking about what trip he wants to do with Overland for next summer. "
What to PackDownload PDF
We travel light at Overland.
- Medium-Sized Duffel Bag or Backpack
3,000-5,000 cubic inch (50-80 liters) duffel bag or backpack.
- 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.
- T-Shirt (1)
- Synthetic T-Shirt (2)
- 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.
- 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.
- 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).
- 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
Comfortable shoes with good traction.
- 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).
- Synthetic Camping Towel
A medium-size synthetic camping towel (synthetic camping towels dry much faster than regular towels).
- Travel Size Toiletries
- Sunscreen (SPF 15+) & Chapstick (with SPF protection)
- Insect Repellent
- Pillow (optional)
Compact, travel-size pillow recommended.
- Camera, Charger & Extra Batteries (optional)
A digital or disposable camera.
- Personal Journal or Book (optional)
- 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 & 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
- We travel light at Overland; please only bring the items on this list.
- 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, bicycles, etc.—on your homeowners insurance policy.
Questions? Call us: 413.458.9672.
What is the weather like on Berkshire Adventure?
You can expect typical summery weather with lots of sunshine, some rain, warm days, and cool nights.
What are the arrival and departure airports for my child’s trip?
Your child will fly to and from Albany International Airport (ALB). We will provide more specific travel information once we have placed your child on a trip. If your child is not flying to the start of the trip, he or she should be dropped off and picked up in Williamstown, Massachusetts.
How often will my child have access to showers?
Nearly every day, and most students shower regularly.
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 for over 30 years. Please click here to read more about our approach to risk management and our accreditation by the American Camp Association.
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.
Please tell me about Overland's admissions process.
When we receive your application, if your first choice is available, we will: (1) call you to acknowledge our receipt of your application, (2) send you an email with a link to our enrollment forms, and (3) charge a deposit of $795 to your credit card. If your first choice is not available, we will call you to discuss options. For more information, and to access our application, please visit our Apply page.
What are Overland’s policies on phones, electronics, and communication?
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 take no responsibility for phones and we will not make any reimbursements for lost, damaged, or stolen phones.
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).
We are committed to providing extraordinary support to you and your child. To that end, the Overland office is staffed from 8:30 a.m. to 8:30 p.m. seven days a week during the summer. Outside of office hours, our answering service provides emergency coverage. Our leaders in the field are in touch 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 then sent back. For this same reason, please do not send mail that requires a signature upon delivery.
4. Please allow one week for postal delivery to U.S. mail stops.
5. Please allow two weeks for postal delivery to international mail stops.
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.
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