Mountains & Sea Adventure
Spend two weeks exploring New England—from the lakes and mountains of New Hampshire to the bike paths and beaches on Martha's Vineyard.
Two weeks packed with friendship and fun.
Swim in Lake Sunapee and hike Mount Monadnock (and enjoy a six-state view from the top). Explore Edgartown, swim at South Beach, and sea kayak quiet bays on the Vineyard. End the trip on a high note with rafting on the Deerfield River. This summer, join Overland for two weeks of adventures in New Hampshire, plus beaches and bike rides on Martha’s Vineyard!
Our trip begins in Williamstown, Massachusetts, with a short afternoon hike to stretch our legs and get to know each other. Then, we’ll travel to New Hampshire’s Lake Sunapee region for hiking, swimming, and camping. Our challenge hike up Mount Monadnock offers a rewarding six-state view from the summit.
We’ll head south to Martha’s Vineyard where we’ll bike around the island on bike paths, visit bustling Vineyard Haven and classic Edgartown, and enjoy picnic lunches and afternoons at the beach. A highlight of our time on the Vineyard will be an afternoon exploring by sea kayak as we paddle quiet bays and coves.
On our last day together, we’ll enjoy a day of rafting on the Deerfield River and then return to Williamstown for a final celebratory dinner where we’ll look back on two weeks of adventure and accomplishment, friendship, and fun.
Mountains & Sea Adventure is a wonderful introduction to exploration and adventure in a supportive, wholesome environment, capably led by caring Overland leaders, with activities carefully calibrated to the interests and abilities of 4th, 5th, and 6th graders.
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).
Fun on the Deerfield River
Bike Path Beauty
Teamwork: Kayaking on Martha's Vineyard
Need to Know
Fun, friends & adventure: the best two weeks of your summer.
Day 1: Trip Start
Our trip starts in Williamstown, Massachusetts. We’ll spend our first afternoon getting to know one another, playing games, and going on a short hike to prepare for our two weeks together.
Days 2-6: Hike in New Hampshire
We’ll drive to New Hampshire’s Lake Sunapee region where we’ll hike, swim, and camp. In the mornings, we’ll hike and explore the countryside. In the afternoons, we’ll swim in beautiful Lake Sunapee, play games, and make new friends. After a few day hikes, we’ll be ready to tackle Mount Monadnock (3,165 feet). We’ll eat lunch at the summit and enjoy the rewarding six-state, 360-degree view of New England.
Days 7-11: Bike, Swim & Kayak on Martha’s Vineyard
We’ll take a break from the trail and drive to Cape Cod. From Woods Hole, Massachusetts, we will take the ferry to Martha’s Vineyard. On the Vineyard, we’ll ride along the bike paths across rolling terrain to classic seaports, charming towns, and long stretches of white sand. As we ride, we will make time to swim, play games, and explore bustling Vineyard Haven and Edgartown. For a change of pace, we’ll take a day to enjoy the island’s coast by sea kayak. Professional guides will teach us the basics of kayaking as we paddle through sheltered coves and inlets.
Day 12: Raft the Deerfield River
We’ll drive back to Williamstown for a whitewater rafting adventure on the Deerfield River with professional outfitters. The Zoar Gap, a spectacular section of the Deerfield River, is a great balance of fun rapids and calmer water.
Day 13: Trip End
Back in Williamstown, we’ll spend our last night celebrating two weeks of fun, accomplishment, discovery, and new friendships.
8 nights of frontcountry camping. Campground facilities will vary and may include flush toilets, hot water, showers, and/or laundry.
4 nights in a hostel or cabins on Martha’s Vineyard.Itinerary may vary by group and is subject to change.
"I loved my leaders! They were fun and always made sure we were having a great time. "
Westfield, New Jersey
"She returned to us a stronger, happier, and braver person. We are so grateful. "
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 (6)
- 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.
- Sleeping Pad
¾-length or full-length closed cell foam (thin and firm) or self-inflating.
- 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 Helmet
If you are flying to trip start, carry your helmet on the plane with you.
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.
- Your group will have access to laundry periodically.
- 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 and sleeping pad with you in case your checked luggage fails to arrive on time.
- 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 Mountains & Sea 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 and laundry?
Nearly every day, and most students shower regularly. Groups will 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 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, raft, and kayak from the mountains of New Hampshire to the beaches of Martha’s Vineyard.
Students going on Mountains & Sea 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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