Writing & Hiking New England

An ideal summer writing program that offers mornings in small classes with inspiring teachers and a proven curriculum followed by afternoons—and a weekend—of hiking and exploring.

Overview Details Itinerary What to Pack FAQs Before You Go


Improve your writing while exploring the Berkshires.

Supportive trip mates, dynamic leaders and experienced teachers: these are the key components of Overland’s writing programs. As an individual writer, you will explore your voice and improve your skills. The class meets in the morning (when everyone is fresh) and works hard for three hours—a significant, sustained engagement with the coursework.

We can’t write all day, so in the afternoon, it’s time to get outside. And what an outside it is: the Berkshires and Vermont’s Green Mountains are ideal for hikes. Of course, the first hikes are shorter and easier, but working at it every day soon increases everyone’s skills and fitness—yours, too.

On the weekend, it’s time to camp and raft. It’s perfect: after a week of great classwork and fun afternoon hikes, we’ll be ready for a change, for more. So we’ll organize the camping gear, pack up and head for the hills. After camping and hiking, we’ll raft the Deerfield River.

During the second week, we’ll pull it all together. Not just the writing (developing a portfolio), and not just the hiking (climbing the tallest mountain in Massachusetts), but the whole experience: learning and fun and friends and everything that makes an Overland summer great. We will realize that the strength of the experience is in the relationships—the friendships that make the hard work fun, that keep spirits up on the trail, that fill every day with laughter and smiles.

You’ll head home a better writer. But just as importantly, you’ll head home more fit, with new friends and fond memories. Writing & Hiking New England—an ideal learning environment, certainly, but more than that, much more than that.

Questions? Contact us!

The perfect combination of academic work, hiking and activities. The kids really connected.

- Kelly Foster, Novato, California

Great morning classes & terrific afternoon hikes.

Day 1: Trip Start

We’ll arrive in Williamstown in the afternoon, unpack, move into our dorm and stretch our legs on an easy hike. Our writing teacher will introduce us to the curriculum, and we’ll do a few pre-writing exercises.

Days 2-6: Writing Class & Hiking the Berkshires & Green Mountains

Every weekday morning, our teacher, with the support of our two leaders, will guide us through the process of expository writing. Together, we will review and learn stylistic and grammatical practices like word choice, paragraph structure and punctuation.

In the afternoons, we’ll explore hiking trails in the Berkshires and Vermont’s Green Mountains. We’ll start small with short hikes to swimming holes and waterfalls, building to more challenging hikes up local mountains and ridges. Some afternoons, we’ll pair a shorter hike with a cultural trip to a local art museum like The Clark or Mass MoCA.

In the evenings, we will cook dinner together, play games and reflect back on the day.

Days 7 & 8: Hike, Camp & Raft 

On the weekend, we’ll leave Williamstown and explore the local mountains. We’ll test our hiking strength on a day hike and then celebrate with a rafting trip down the Deerfield River with professional guides. We’ll spend our nights at an established campground, learning the basics of camping.

Days 9-13: Writing Class & Hiking the Berkshires & Green Mountains 

After a weekend outside, we will return to Williamstown for our final four days of morning classes and afternoon hikes. We’ll apply skills learned during our first week of class as we write an expository essay inspired by National Public Radio’s This I Believe. We’ll brainstorm, outline, write a first draft, read out loud, edit, revise and produce a final product in a supportive and encouraging environment. On our last day of class, we will compile all of our work into a comprehensive writing portfolio.

Throughout our final week, we’ll continue to grow as hikers and prepare for a challenge hike up Mount Greylock, the highest mountain in Massachusetts. At the summit, we will appreciate the views and reflect on a fantastic two weeks together.


10 nights in a dormitory on the Williams College campus.

2 nights of frontcountry camping with access to flush toilets and hot water.

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

We travel light at Overland!


  • Medium-Sized Duffel Bag
    3,000-5,000 cubic inch (50-80 liters) suitcase or duffel bag.


  • 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 (4)
  • Synthetic Shorts (3)
  • Pants (1)
    Suitable for day hikes, class and cool evenings.
  • Synthetic Long Underwear Top & Bottom (1)
  • Underwear (7)
  • Athletic Socks (5)
  • Wool and/or Synthetic Socks (4)
  • 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.

General Gear

  • 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


  • Waterproof Hiking Boots
    Hiking boots that are low to high cut, depending on your desired ankle support. Choose comfortable boots and make sure to break them in before the start of your trip.
  • Sneakers
    Comfortable shoes with good traction.
  • Water Shoes
    Closed-toed sport sandals, water shoes or old sneakers to wear on the water.
  • Sandals (optional)
    Flip flops or Crocs work well.


  • Extra Long Twin Linens
    One to two sets of linens. A pillow, mattress pad and blanket are provided.
  • Small Bath Towel
  • Beach Towel
  • Travel Size Toiletries
  • Sunglasses
  • Sunscreen (SPF 15+) & Chapstick (with SPF protection)
  • Room Fan (optional)
    The Williams College dorms are not air-conditioned. Overland will have some fans available. If you are arriving by car, we encourage you to pack a small fan.
  • USB Flash Drive
    1 GB of memory to save your writing projects at trip end.
  • 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).
  • There are no reimbursements for lost, damaged or stolen items.
    Please schedule expensive items—phones, cameras, bicycles, etc.—on your homeowners insurance policy.
  • Overland provides you with a laptop. If you have writing samples you want to bring with you, bring those documents on a flash drive or as a hard copy.

Questions? Call us! 413.458.9672

  • Who will my child have for a writing teacher?

    Overland partners with professional teachers who typically hold a masters in English or Education and taught or currently teach at the middle school or high school level. Many of our teachers have previously taught the Writing & Hiking New England class, and they create a supportive, fun environment for students to flourish as writers. Past teachers include:

    Cynthia Saunders Quiñones is a poet and teacher living in Berkshire County. She has taught literature and writing in a classroom setting for more than 16 years. She holds a B.A. in English and creative writing from George Washington University, and an M.F.A. in poetry from the Warren Wilson College Program for Writers, where she was a Rona Jaffe Fellow. She currently serves as an artistic mentor for Barrington Stage Company’s Playwright Mentoring Project, as well as a workshop facilitator for the Northern Berkshire Community Coalition’s Teen Writing Workshop. In 2016, she received a Martha Boschen Porter Fund Grant from the Berkshire Taconic Community Foundation to complete a first book length manuscript. Her own poems and articles have been published in various journals in print and online. Cynthia is returning to teach the Writing & Hiking New England class for her second summer.

    Mallory Tarses has taught high school English for 18 years in Los Angeles, California and Wilmington, North Carolina. In September, she will begin her 15th year at Cape Fear Academy, teaching American Literature, AP Language, and SAT Preparation courses. She received her B.A. from Brown University, her M.F.A. from The Johns Hopkins Writing Seminars, and her M.A. in Fiction Writing from the University of North Carolina at Wilmington. Her short stories have appeared in Ploughshares, the North American Review, the Kansas Quarterly/Arkansas Review and other literary magazines. Mallory is returning to teach the Writing & Hiking New England class for her seventh summer.

    Rebecca Tucker-Smith has taught middle and high school English at Mt. Greylock Regional School for nine years. She received a B.A. in English and Fine Arts from Amherst College and a M.S. in Education from the University of Oregon. While Rebecca has taught a variety of grade levels, she current teaches AP Language and Composition in addition to serving as the Curriculum Leader for the English department. An avid reader and an enthusiastic writer, Rebecca considers herself a lifelong learner and is returning to teach the Writing & Hiking New England class for her second summer.

  • What is the weather like on Writing & Hiking New England?

    You can expect typical summery weather with lots of sunshine, some rain, warm days and cool nights.

  • How often will my child have access to showers and laundry?

    Your child’s group will have access to showers and laundry regularly.

  • 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.

  • 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 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.

Get ready for a week full of fun, friends & learning.

Students going on Writing & Hiking New England should prepare for:

  • Full afternoons of outdoor activities led by two caring Overland leaders
  • Day hikes to viewpoints and mountaintops
  • A weekend hiking, rafting and camping trip
  • 9 days of writing class for 4 hours each morning
  • 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 Writing & Hiking New England, you will go on a total of 10 day hikes. You will hike on well-established trails in New England through a variety of landscapes, including forests and more open alpine environments. You will travel over terrain ranging from gentle and rolling to rocky and steep. In the month before your trip, 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 will help to make the trip a success for you... and for everyone in your group.

Pre-trip Training:

  • 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 .
  • 1 week before your trip: take two 2-hour hikes or walks in your boots .

Preparing for Class

Overland classrooms are small, supportive and focused—you will spend four hours each weekday morning working with a master teacher and two Overland leaders. You should arrive excited about writing and ready to work hard to improve your writing skills. While we do not require a specific level of writing or any pre-trip writing materials, we expect you to engage in our writing curriculum. During your trip, Overland will provide the curriculum, writing prompts and laptops. All you need is your enthusiasm, energy and a flash drive to save your work.

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.