“I really like how the groups are formed without most campers knowing each other. I think it’s great to teach the campers how to make new relationships.” ~ Kim Mehrara, Rye, New York
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, slower, simpler 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 setting, 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 are focused on building confidence and independence during their time with Overland.
We’ll begin with easier hikes and walks, building up to our hike of Mount Greylock, the highest point in Massachusetts. We’ll also spend a day cycling the quiet, car-free Ashuwillticook Rail Trail and enjoy a day of rafting on the Deerfield River.
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 (and with caring leaders providing excellent supervision to a small group of very nice kids). The activities are fun and the tone is always warm and welcoming, positive and enthusiastic. Berkshire Adventure has always been a great success for us—and it can be for your child, too.
Overland's ability to create age-appropriate challenges in a warm environment makes it our first choice.
- Amy Selinger, Lexington, Massachusetts
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 fun games and a short, beautiful hike.
Days 2-4: Exploring the Berkshires
On our first 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. During our second day, we’ll head south to bike along the Ashuwillticook Rail Trail—an old railroad corridor converted to a bike path (22 miles total). Between hikes and rides, 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 fun hike guided by the Williamstown Rural Lands Foundation.
Day 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.
Day 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, fun 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.
Things to know
- We travel light on Overland trips; please only bring items on your packing list.
- Please do not bring any electronics (including your cell phone). See FAQs 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 start, 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 wear the navy Overland shirt that you will receive from the Overland office to your trip start location.
- Medium-Sized Duffel Bag or Backpack
3,000-5,000 cubic inch (50-80 liters) duffel bag. You will leave the duffel bag and any extra items in our van during the trip and use your day pack for hikes and daily activities.
- Navy Overland Shirt (1)
We will send students an Overland shirt prior to their trip, and we encourage students to wear their Overland shirt to trip start. We highly recommend this for students flying to their trip start location.
- T-Shirt (4)
Short-sleeve T-shirt or tank top.
- Long-Sleeve T-Shirt (2)
Lightweight for sun protection.
- Synthetic Shorts (3)
- Pants (1)
Suitable for cool evenings in camp (synthetic pants are preferred).
- Underwear (6)
- Athletic Socks (pair) (4)
- Swimsuit (1)
- Hat with Visor (1)
For protection from the sun. Baseball hats are acceptable.
- Winter Hat (1)
- Pajamas (optional)
Students sometimes prefer to sleep in shorts and a T-shirt instead of bringing pajamas.
- Waterproof Raincoat (1)
Waterproof material required (not just water resistant). Rain coats provide protection from wind and rain and serve as an extra warm layer. Your jacket should be large enough to allow layers underneath. We recommend hoods and breathable materials. Gore-Tex is a well-known waterproof and breathable fabric but there are many other quality fabrics. Ponchos are not acceptable.
- Fleece Jacket or Pullover (1)
Medium to heavyweight and reasonably compact.
- 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 & Extra Batteries
Headlamps are preferable because they free up your hands.
- 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).
- Water Bottle
One 1-liter bottle (a smaller size is acceptable).
- Bike Helmet
If you are flying to trip start, carry your helmet on the plane with you.
- Sneakers (pair)
Comfortable shoes to wear on daily activities. Shoes should be supportive and have a good tread on the bottom for 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).
All items should be travel size (if necessary, you will be able to restock during the trip).
Polarized sunglasses that wrap around to protect from glare are ideal.
- Sunscreen (SPF 15+) & Chapstick (with SPF protection)
- Spending Money
$30 per week in cash or a debit/ATM card.
- Pillow (optional)
Compact, travel-size pillow recommended.
- Camera, Charger & Extra Batteries (optional)
A digital or disposable camera and, if necessary, a charger and large enough memory card to accommodate your pictures (4 to 8 GB).
- Personal Journal or Book (optional)
- Health Insurance Card
Please bring an original or copy of your health insurance card.
- What is the weather like on Berkshire Adventure?
The weather on Berkshire Adventure varies. Sometimes it is sunny and warm, other times it is rainy and cold; average summer temperatures range from 50s to 80s and may be cooler at night. Our packing list takes these variables into consideration. Layering is the best strategy. Please follow the packing list, paying close attention to rain gear specifications.
- 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 program. 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?
While we have regular access to showers, most students will shower once or twice during the trip.
- 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 and other 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 his or her interests and abilities. You should spend some time familiarizing yourself with the details of the specific program 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 where each group member feels welcomed and valued.
- Please tell me about Overland’s admissions process.
For more information, and to access our application, please visit our Apply page.
When we receive child’s application, if the first choice is available, you will receive a phone call and an email containing a link to our Overland Portal where you will find our Admissions Review Forms. We will accept your deposit to hold your child’s place in the program pending a favorable Admissions Review. If the first choice is not available, we will call you to confirm that the second choice is acceptable. If neither the first choice nor second choice are available, we will call you to discuss options. For those students placed on our waitlist, we will notify you as soon as a spot becomes available.
We seek to admit students who have demonstrated that they possess the personal qualities and experience necessary to succeed on an Overland trip. While Overland is always supportive and nurturing, an Overland program is unlike a traditional camp in that our small groups–12 students and 2 leaders–travel, live and work as a group, making all of their own meals, helping each other and cooperating in ways big and small, and they do all of this far from home. As a result, every student must be able to thrive in an environment that places equal emphasis on:
1. Teamwork and Shared Responsibilities.
2. Independence and Self-Reliance.
3. Support of Others and Consideration for Others.
- 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 (the exceptions to this are: 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 him or her with an expensive smartphone; instead bring an inexpensive prepaid cell phone. 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.
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 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.
Hike, bike, and raft in the Berkshires of Massachusetts.
Students going on Berkshire Adventure should prepare for:
- 5 days of outdoor exploration for several hours each day
- Travel to and from the trip
- An Overland experience
We expect you to arrive to your trip fully prepared for all activities.
Preparing for Travel to and from the Trip
Families are responsible for arranging flights to and from the designated airport during a specified window (please do not purchase flights until you have received an email confirming our review of your health forms and school reference). Overland staff will be at the airport to welcome you at the start of your trip and to assist with your departure. If you are not flying to and from your trip, you should be dropped off and picked up in Williamstown, Massachusetts. If you are flying to and from your trip, we will have you call home upon arrival and before departure. We will provide more specific travel information once we have placed you on a program.
Preparing for an Overland Experience
Overland programs are wholesome, structured experiences with high expectations of each student’s behavior. You are expected to be supportive of your trip mates and your leaders, enthusiastic, positive and helpful. We ask that you leave your cell phone and electronics at home (cameras are always welcome), so you can fully engage with your group and your trip. You will have the opportunity to send letters and receive mail at designated mail stops, which are shared in the spring.
Arriving ready for a challenge, eager to experience new activities, and prepared to contribute to an enthusiastic group will go a long way toward creating a successful trip. Please contact us if you’d like to discuss preparing for your Overland program.