Writing & Hiking New England

Overview Details Itinerary What to Pack FAQs Before You Go


Supportive trip mates, dynamic leaders, experienced teachers, an impressive college campus and rolling New England mountains: 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 come 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 (which is really, really fun).

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 enliven 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 writing program was phenomenal. Our teacher was amazing.

- Brian Phillips, New York, New York
Itinerary may vary by group and is subject to change.


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 master 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 experienced 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 will 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 writing, revising and hiking. We will apply skills learned during our first week of class as we write an expository essay inspired by National Public Radio’s This I Believe essay. We will brainstorm, outline, write a first draft, read out loud, edit, revise and produce a final product in a fun 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 will continue to grow as hikers and prepare for a challenging hike up Mount Greylock, the highest mountain in Massachusetts. At the summit, we will appreciate the views and reflect on a fun 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.

Download PDF

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).
  • There are no reimbursements for lost, damaged or stolen items.
  • 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.
  • Please wear the navy Overland shirt that you will receive from the Overland office to your trip start location.


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


  • 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.
  • Pants (1)
    Suitable for day hikes, class and cool evenings.
  • Synthetic Shorts (3)
  • T-Shirt (4)
    Short-sleeve T-shirt or tank top.
  • Synthetic Long Underwear Top & Bottom (1)
  • Athletic Socks (pair) (5)
  • Wool and/or Synthetic Socks (4)
  • Underwear (7)
  • Pajamas (1)
    Students sometimes prefer to sleep in shorts and a T-shirt instead of bringing pajamas.
  • Swimsuit (1)

Outer Layers

  • 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.

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 & 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).


  • 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 (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 (pair) (optional)
    Flip flops or Crocs work well

Travel Documents

  • Photo Identification
    A current school or other kind of photo identification (if you have one).
  • Unaccompanied Minor Fee Receipt (if applicable)
    For students travelling as Unaccompanied Minors, please print a copy of the UAM fee receipt for your child's leaders to keep on file.
  • Baggage Fee Receipt (if applicable)
    Some airlines allow passengers to input credit card information to cover checked bag service charges when checking in online prior to the trip. To reduce hassle at the airport, we encourage you to pay for checked baggage beforehand and supply your child with a copy of the receipt for his or her leaders to keep on file.


  • Extra Long Twin Linens
    One to two sets of linens. A pillow, mattress pad and blanket are provided.
  • Small Bath Towel
    For showering
  • Toiletries
    All items should be travel size (if necessary, you will be able to restock during the trip).
  • Sunscreen (SPF 15+) & Chapstick (with SPF protection)
  • Sunglasses
    Polarized sunglasses that wrap around to protect from glare are ideal.
  • Beach Towel
  • Spending Money
    $30 per week in cash or a debit/ATM card.
  • USB Flash Drive
    1 GB of memory to save your writing projects at trip end.
  • Personal Journal or Book (optional)
  • 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.
  • 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).
  • Health Insurance Card
    Please bring an original or copy of your health insurance card.
  • 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. Possible teachers include:

    Trudy Ames has taught a mix of literature and writing to students with a wide range of interests and abilities as an English teacher for 25 years at Mount Greylock Regional School in Williamstown, Massachusetts. She received her B.A. in English from the University of Massachusetts in Amherst, a combined M.Ed./English degree from the University of Massachusetts in Amherst and an M.F.A. in writing from Bennington College in Bennington, Vermont. A writer herself, Trudy’s work has been published in numerous anthologies and magazines.

    Rebecca Leonard has been a teacher of third through fifth grade at Williamstown Elementary School for 22 years, where she particularly enjoys teaching writing. She received a B.A. in Literary Studies with French from Williams College and an M.Ed. from Smith College. Prior to teaching, she worked in educational publishing at Scholastic, Inc. She looks forward to working with middle schoolers who are excited to take inspiration from the beautiful Berkshires.

    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 15 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.

    Julie Schutzman has taught English at Miss Hall's School in Pittsfield, Massachusetts, for the past ten years, where she spent six years as department chair. She is currently the director of the school's writing center and loves working one-on-one with students on writing projects of all kinds. She received a B.A. and M.A. in English from Brown University and a Ph.D. in English and American Literature from the University of Pennsylvania. She is excited to share her love of summer in the Berkshires with a group of young writers.

    Rebecca Tucker-Smith has taught middle and high school English at Mt. Greylock Regional School for eight 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 looks forward to teaching the Writing & Hiking New England class this summer.

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

    The weather on Writing & Hiking New England 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.

  • 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 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.

  • 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. 1. Teamwork and Shared Responsibilities. 
    2. 2. Independence and Self-Reliance. 
    3. 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.

  • 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 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.

Improve your writing while hiking and exploring the Berkshires and Vermont’s Green Mountains.

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

  • 10 days of hiking with an average of 5 miles per day
  • 9 days of writing class for 4 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 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.

Before your trip, we strongly advise you spend time breaking-in and adjusting to your hiking boots. Please follow our guidelines as you prepare for your program.

Pre-trip training:

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

While hiking, the pace of your group will vary. Typically, you will take multiple breaks over the course of the hike - for water, snacks, lunch, to adjust packs, etc.

Preparing for Class

Overland classrooms are small, supportive and focused—you will spend four hours per weekday 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 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 improve your writing skills 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.