Explore the best of New England by foot and kayak.
Designing a two-week hiking trip is simple really. First, we consider the students: many are first-timers at this kind of thing. So we calibrate the trip and pace appropriately. Then we need a beautiful area to explore. New England Explorer hits the mark in all these ways—good for first-timers, just the right pace and a beautiful place. See, it’s simple. Really.
Start with day hikes. No heavy packs—just lunch and water—and a reasonable goal. On New England Explorer, we start in the Berkshires and the Green Mountains, where green hills become mountains, and there’s a perfect balance of challenge and fun.
Over time add more challenge. Take on Vermont’s larger mountains —still a day hike, but higher and longer. Then head to New Hampshire’s White Mountains—craggy, handsome peaks with a rich and storied history—for three days of backpacking. Top it off with a hike to the top of Mount Washington, at 6,289 feet the highest point in New England—a great adventure and an ideal challenge.
Then mix it up and try something new. Head to the coast of Maine for two days of sea kayaking. Paddling is a great way to explore the area, offering a close look at the bays and islands of this famous and picturesque coastline.
At trip end, celebrate everything—the adventures and accomplishments, the friendships and fun. Now that’s a nice trip.
My favorite part was backpacking and climbing Mt. Washington. It was so pretty, and I felt accomplished.
- Dexter Mayo, Pacific Palisades, California
Days 1 & 2: Trip Start and Hike in the Berkshires
After meeting in Williamstown, Massachusetts, we’ll spend two days camping and hiking in the Berkshires and Vermont’s Green Mountains. We’ll celebrate our first few days of hiking with lunches on summits or at beautiful vistas while taking in panoramic views.
Days 3 & 4: Hike in Vermont’s Green Mountains
We’ll head north to the heart of Green Mountains and go on a series of hikes that will build our endurance and strength. During our days in Vermont, we also will find time to swim in pristine mountain lakes and the Ben & Jerry’s ice cream factory.
Days 5-8: Backpack in New Hampshire’s White Mountains
In the rugged White Mountains of northern New Hampshire, we’ll don our backpacks for a three-day backcountry hike. We’ll walk along ridgelines, enjoy spectacular panoramic views and prepare for our climb up Mount Washington (6,288 feet), the highest point in the Northeast. We’ll ascend via the fabled Tuckerman’s Ravine trail to enjoy the summit’s sweeping views of the Presidential Range.
Days 9-11: Sea Kayak Coastal Maine
Near the end of our trip, we’ll spend two days kayaking and enjoying the peaceful beauty of coastal Maine. We’ll tour the rocky coves, secluded bays and wild islands of this picturesque coastline.
Day 12: Trip End
At trip end, we’ll return to Williamstown and look back on two weeks of outdoor exploration. We’ll celebrate our adventures, our accomplishments and the friendships we formed along the way.
9 nights of frontcountry camping. All campgrounds will have access to hot water and flush toilets. Some facilities may include showers and laundry.
3 nights of backcountry camping at established campsites. Campsites may have a primitive, small shelter and an outhouse.
Things to know
- We travel light on Overland trips; please only bring items on your packing list.
- Your group will have access to laundry periodically.
- 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, wear your hiking boots and carry your sleeping bag and sleeping pad on the plane in case your checked luggage fails to arrive on time.
- Pack everything in your backpack or day pack. Do not bring additional luggage.
- 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.
- 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.
- 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.
- Synthetic Long Underwear Top & Bottom (1)
- Winter Hat (1)
- Gloves or Mittens (pair) (1)
To stay warm in camp on cool nights.
- Synthetic Shorts (3)
- Synthetic T-Shirt (3)
Short-sleeve T-shirt or tank top.
- Underwear (5)
- Wool and/or Synthetic Socks (3)
- Swimsuit (1)
- Pajamas (optional)
Students sometimes prefer to sleep in shorts and a T-shirt instead of bringing pajamas.
- Hat with Visor (optional)
For protection from the sun. Baseball hats are acceptable.
- Fleece Jacket or Pullover
Medium to heavyweight and reasonably compact.
- Waterproof Raincoat
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.
- Waterproof Rain Pants
Waterproof material required (not just water resistant). Rain pants provide protection from wind and rain and serve as an extra warm layer.
- Insulated Vest
Insulated fleece, Thinsulate or down vest to wear on cold days and evenings.
- Internal Frame Backpack
50-70 liters or 3,000-4,300 cubic inches (if you plan to do longer backpacking trips in the future, consider purchasing a pack that is towards the higher end of this range). Before purchasing a backpack, find your backpack size by measuring your torso length and your hips (instructions are available here). We recommend getting fitted at a store and trying on multiple packs.
- 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
A lightweight, compact sleeping bag rated to 30 degrees Fahrenheit or less. We recommend either synthetic or treated down material. Your sleeping bag should compress into a stuff sack no larger than 20" in length.
- Sleeping Pad
Full- or ¾-length compact sleeping pad. We recommend closed cell foam that is thin and firm (e.g., RidgeRest) or self-inflating (e.g., Therm-a-Rest).
- 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).
- Headlamp & Extra Batteries
- Waterproof Pack Cover
If your backpack does not come with a cover, we recommend buying a cover one size larger than your pack.
- Water Bottle
One 1-liter bottle. A Camelbak or similar water carrier is acceptable.
- Waterproof Hiking Boots
Choose comfortable boots designed for hiking with a pack (i.e., mid to high cut for ankle support). Boots should be waterproof. Break them in before the start of your trip.
- 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).
- Camp Shoes
Closed-toe shoes to wear around camp. Crocs or lightweight tennis shoes are ideal.
- Photo Identification
A current school or other kind of photo identification (if you have one).
- Synthetic Camping Towel
A medium-size synthetic camping towel (synthetic camping towels dry much faster than regular towels).
- Gallon Sized Ziploc Bags (10)
To organize and waterproof your gear and small items.
All items should be travel size (if necessary, you will be able to restock during the trip).
- Package of Moleskin or Molefoam (1)
To protect your feet from blisters.
Polarized sunglasses that wrap around to protect from glare are ideal.
- Sunscreen (SPF 15+) & Chapstick (with SPF protection)
- Insect Repellent
- Camera, Charger & Extra Batteries
A digital or disposable camera and, if necessary, a charger and large enough memory card to accommodate your pictures (4 to 8 GB).
- Spending Money
$30 per week in cash or a debit/ATM card.
- 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 New England Explorer?
The weather on New England Explorer varies. Sometimes it is sunny and warm, other times it is rainy and cold; average summer temperatures range from the 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?
You will need to arrange transportation for your child to and from Albany International Airport (ALB) at trip start and end. 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. We will provide more specific travel information once we have placed your child on a program.
- How often will my child have access to showers and laundry?
Groups typically shower and do laundry once a week.
- 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, backpack and sea kayak from the mountains of Massachusetts, Vermont and New Hampshire to the coast of Maine.
Students going on New England Explorer should prepare for:
- 6 days of hiking with an average of 6 miles per 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 Hiking
On New England Explorer, you will go on three day hikes and spend a total of three days backpacking. You will hike on well-established trails through a variety of landscapes, including forests and more open, rocky terrain. While New England Explorer is designed as an introduction to backpacking, the hiking will be challenging at times.
Backpacking is a strenuous physical activity and requires proper training. While backpacking, our groups are fully self-supported—you will carry all of your belongings (clothes, sleeping bag and pad), some group gear, food and water. Your leaders will distribute group gear and food among all members of the group. Pack weights will vary trip by trip, depending on the location, weather, student and the distance covered. Typically when backpacking, pack weights average about 30% of a hiker’s weight.
Before your trip, we strongly advise you spend time breaking-in and adjusting to your hiking boots or shoes. Please follow our guidelines as you prepare for your program
- 5 weeks before your trip: wear your boots for 15-30 minutes a day. Walk around your house or neighborhood so your boots begin to conform to your feet.
- 4 weeks before your trip: take three 30-minute hikes or walks in your boots.
- 3 weeks before your trip: take three 1-hour hikes or walks in your boots.
- 2 weeks before your trip: take three 1-hour hikes or walks in your boots with a backpack loaded with 10% of your body weight.
- 1 week before your trip: take two 2-hour hikes or walks in your boots with a backpack loaded with 15-20% of your body weight.
Groups typically average between 1½ and 3 miles per hour (although pace varies by group). You will take multiple breaks in the morning and afternoon—for water, snacks, lunch, to adjust packs, etc.
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. Overland expects all students to contribute to an enthusiastic, positive group. We expect you to be helpful and supportive of your trip mates and leaders. 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.
All trips have a range of challenges. You should come prepared and recognize that some days will be more difficult, more challenging and longer—both in terms of miles and hours on the trail—than others. Delays occur due to a wide range of variables beyond the control of you, your group or your leaders. Weather patterns change and trail and route conditions vary. You, or someone in your group, might develop a blister or encounter another issue that could delay your group. On some days your group will arrive into camp in the early afternoon, with plenty of time to explore the area or go swimming, while on other days your group will spend more time on the trail.
Arriving ready for a challenge—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.