New England Explorer

For two weeks, explore Massachusetts' Berkshire Hills, Vermont's Green Mountains and New Hampshire's White Mountains. Hike to the highest points in each state, developing skills and fitness while having fun and making friends. Off the trail, head to the coast of Maine for sea kayaking and experience the beauty of New England from a different, and equally stunning perspective.

Overview Details Itinerary What to Pack FAQs Before You Go

Overview

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, it’s 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 friendship and fun. Now that’s a nice trip.

Questions? Contact us!

Thank you for the best two weeks of my life!


- Ashley Clemens, Larchmont, New York

The best two weeks of exploring in New England.

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 visit 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.

 

ACCOMMODATIONS 

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.

Itinerary may vary by group and is subject to change.
Download PDF

We travel light at Overland.

Luggage

  • 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.

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)
  • 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.
  • Synthetic Long Underwear Top & Bottom (1)
  • Underwear (5)
  • Wool and/or Synthetic Socks (4)
  • Gloves or Mittens (1)
  • Winter Hat (1)
  • Hat with Visor (1)
  • Swimsuit (1)
  • Pajamas (optional)
    Students sometimes prefer to sleep in shorts and a T-shirt instead of pajamas.

Outer Layers

  • Fleece Jacket or Pullover (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.
  • Waterproof Rain Pants (1)
  • Insulated Fleece or Down Vest (1)

General Gear

  • Waterproof Pack Cover
    If your backpack does not come with a cover, we recommend buying a cover one size larger than your pack.
  • 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).
  • Synthetic Sleeping Bag
    A lightweight, compact synthetic sleeping bag rated to 30 degrees Fahrenheit or less. A synthetic sleeping bag is required for this trip; down is not appropriate as it does not insulate if wet. Your sleeping bag should compress into a stuff sack no larger than 20" in length.
  • Sleeping Pad
    ¾-length or full-length closed cell foam (thin and firm) or self-inflating.
  • 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
    Please bring an extra battery/batteries.
  • Water Bottle
    One 1-liter bottle. A Camelbak or similar water carrier is acceptable.

Footwear

  • 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.

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)
  • Insect Repellent
  • Gallon Sized Ziploc Bags (10)
    To organize and waterproof your gear and small items.
  • Large Trash Bags (4)
    To waterproof your gear.
  • Package of Moleskin or Molefoam
    To protect your feet from blisters.
  • 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

  • We travel light at Overland; please only bring the items on this list.
  • Your group will have access to laundry periodically.
  • Please do not bring your smart phone (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, 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 schedule expensive items—phones, cameras, bicycles, etc.—on your homeowners insurance policy.

Questions? Call us: 413.458.9672.

  • What is the weather like on New England Explorer?

    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?

    You will need to arrange transportation for your child to and from Albany International Airport (ALB) at trip start and end. 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 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 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 where each group 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 Admissions Review Forms, and (3) charge a deposit of $795 to your credit card to hold your place in the trip pending a favorable admissions review. If your first choice is not available, we will call you to discuss your second choice, third choice or other options. For more information, and to access our application, please visit our Apply page.

  • 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 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 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.

Hike, backpack and sea kayak the best of New England.

Students going on New England Explorer should prepare for:

  • Full days of outdoor activities led by two caring Overland leaders
  • Day hikes to viewpoints and mountaintops
  • A multi-day backpacking trip designed for first-time backpackers
  • A fun, supportive and wholesome Overland experience

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

Preparing for the Hiking

On New England Explorer, you will hike on well-established trails over a wide range of terrain, from meadows to hills to mountains. You'll start with day hikes where you'll carry just the essentials for the day (snacks and lunch, water, a hat, sunglasses and sunscreen, bug spray, and a raincoat). As the group's skills and fitness increase, you'll set out on a multi-day backpacking trip. While backpacking, you will carry all of your belongings (clothes, sleeping bag and pad), some group gear, food and water. Typically when backpacking, pack weights average about 30% of a hiker's weight. In the month before your trip starts, you should break-in your hiking boots (wear them a lot!) and complete the pre-trip training (see below). Once on your trip, you'll find that enthusiasm and a positive attitude on your part will help to make the trip a success for you... and for everyone in your group.

Pre-trip Training:

  • 4 weeks before your trip: three 45-minute hikes or walks in your boots.
  • 3 weeks before your trip: three 60-minute hikes or walks in your boots.
  • 2 weeks before your trip: three 90-minute hikes in your boots with a backpack loaded with 10% of your body weight.
  • 1 week before your trip: four 2-hour hikes in your boots with a backpack loaded with 20% of your body weight.

Preparing for an Overland Experience

Overland trips are wholesome, structured experiences with high expectations of each student’s behavior. You are expected to be enthusiastic, positive, helpful and supportive of your trip mates and your 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. 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 trip.