We Welcome Your Application to Join Us!
We build each of our groups with care, keeping the groups small (no more than twelve students), and paying close attention to age, grade, gender, and the mix of hometowns and schools. Our goal is to put together great groups — groups where nice kids thrive in a supportive, wholesome, and caring environment. Please note: availability as shown is based on students traveling without a friend; if your child is interested in traveling with a friend, please call our office for availability.
Important Information about Availability
This departure of this trip has good availability. Apply as soon as possible since availability changes quickly.
This departure of this trip has limited availability. Apply as soon as possible, and on receipt of your application, if space is still available, we’ll confirm a spot for you. If all of the spots are taken, we’ll call you to discuss options.
This departure of this trip is currently full — please call us to discuss options.
How to Apply
Apply online using a credit card for the $795 deposit (your card will not be charged until we confirm a spot for you). Applications are reviewed in the order in which they are received (we do not hold spots over the phone).
When to Apply
The flow of applications starts in July and peaks in January/February. Some groups fill by the December holidays, and others will have space into the late spring. Our advice? Apply as soon as possible — it only takes a few minutes — and we’ll get to work right away to find a great spot for you.
Call (413.458.9672) or email (email@example.com). We look forward to hearing from you.
Ride the length of Vermont (and have a blast doing it!).
Vermont in the summer—perfect!
Bike along green fields, by red barns, and past white-steepled churches on Vermont’s beautiful back roads.
Biking is fun — really fun — because we do it with a group of new friends. We take our time — it isn’t a race. We stop a lot — for water and snacks and lunch and, yes, for Ben & Jerry’s.
The camping is fun, too, and so are the games and the kayaking. Come to think of it, it’s all fun. That’s the point — two weeks of fun, with new friends and two great Overland leaders.
The kids who come are adventurous, enthusiastic, and friendly. And a lot of them — most of them actually — have never been on a bike trip before. That’s okay. Everyone learns quickly, and our Overland leaders are there to motivate, encourage, and support — every mile of the way from Massachusetts to Canada.
Green Mountains in the Distance
Ready to Ride!
Kayaking on Lake Champlain
Friends & Ice Cream
Need to Know
Included in Trip Fee
- Group gear
- Albany International Airport shuttle
Fun, friends, challenge, and accomplishment.
Day 1: Trip Start
We’ll meet in Williamstown, Massachusetts, and drive a short distance to our first campground. In the afternoon, we’ll prepare for our bike trip, learn how to load our bikes, and practice riding as a group.
Days 2-6: Southern Vermont
On the border of Massachusetts and Vermont, we’ll start our trek north. We’ll bike through farms and rural communities in the valley between the Green Mountains and the Adirondacks. The terrain is gently rolling and increases in difficulty as we build up strength each day. We’ll make our way through southern Vermont, spending nights in campgrounds from the shores of Lake Shaftsbury and Lake St. Catherine to the unhurried, unspoiled town of Brandon.
Days 7-11: Kayak Lake Champlain & Explore Burlington
From Brandon, we’ll ride to the southern end of Lake Champlain. Our route skirts along the shores of the lake with views of the Adirondacks to the west and the Green Mountains to the east. The lively town of Burlington provides a nice change of pace from the small Vermont communities we will have ridden through in days past. We’ll spend a day kayaking on Lake Champlain and exploring the town as we prepare for our remaining trek to the border. As we continue north, we’ll ride the length of South Hero Island.
Days 12 & 13: The Canadian Border & Trip End
Our trip comes to an end after crossing North Hero Island into Alburgh. After two weeks on our bikes, we’ll ride triumphantly to the Canadian border. We’ll then drive back to Williamstown and celebrate the accomplishment of biking the entire length of Vermont.
12 nights of frontcountry camping. Campground facilities will vary and may include hot water, flush toilets, showers, and/or laundry.Itinerary may vary by group and is subject to change.
"I loved reaching the border and feeling accomplished. "
Cranbury, New Jersey
"Eve had a wonderful experience. The leaders were supportive and engaging. "
Port Washington, New York
What to PackDownload PDF
We travel light at Overland.
- Medium-Sized Duffel Bag or Pair of Panniers
Panniers are saddlebags sold in pairs that attach to either side of your rear rack. If you are renting panniers from Overland, pack your belongings in a collapsible bag (3,000-5,000 cubic inch/ 50-80 liters). We will have your bag available at the end of the trip for travel home. The cost of renting panniers from Overland is included in a bike rental (or they can be rented separately for $50). If you are bringing your own panniers you will want large panniers, 2,400-3,000 cubic inches (40-50 liters) total, designed for bike touring. One large pannier has internal dimensions of approximately 17" x 13" x 7". You should be able to fit all of your belongings, besides your sleeping bag and pad, into your two panniers and have some space for group gear. If flying to trip start, you can tape your panniers together so that they count as a single piece of checked luggage.
- 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 High-Visibility T-Shirts (3) & Vest (1)
A high-visibility outer layer is required at all times while biking (high-visibility is a neon or fluorescent color, typically yellow, orange or pink). On warm days a high-visibility T-shirt will be sufficient. The vest should be large enough to wear over warm layers while riding on cooler days. High-visibility bike jerseys are acceptable but not necessary.
- T-Shirt (1)
- Lightweight Long-Sleeve T-Shirt (1)
- Shorts for Biking (2)
Synthetic material recommended (some students bring padded, spandex bike shorts but they are not required).
- Shorts (1)
Comfortable shorts to wear around camp.
- Fleece Pants (1)
Please do not bring cotton sweatpants (they are heavy and bulky and will not keep you warm if wet).
- Underwear (5)
- Athletic Socks (4)
- Wool and/or Synthetic Socks (1)
- Swimsuit (1)
- Pajamas (optional)
Students sometimes prefer to sleep in shorts and a T-shirt instead of pajamas.
- 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. Choose high-visibility if available.
- 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
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).
- Water Bottle
A 24-ounce bike bottle is ideal (on arrival you will receive a second bottle from us).
- Hydration System (optional)
A small backpack with a bladder inside (e.g., CamelBak or Platypus) works well. If you bring a backpack, it must be a high-visibility color; if the bag is not hi-vis, you must cover it with hi-vis fabric or tape. The backpack should be designed primarily to carry water (if it is too big or filled with other items, it will be uncomfortable to wear all day).
- Touring Bicycle & Rear Rack
You may choose to rent a bicycle and rear rack from Overland to use during your trip or you can bring your own. Please see the Right Bicycle for Your Overland Trip for more information about acceptable bikes and traveling with your bike. Please note: the American Challenge, European Challenge and Canadian Rockies & Montana 2-week require specific bikes—keep this in mind if you are buying a new bike now and plan on doing one of these trips in a future summer.
- Bike Helmet
If you are flying to trip start, carry your helmet on the plane with you.
- Rear Bike Light
A rear bike light is required—both when you train in the spring and once you are on your Overland trip in the summer. The light can be USB or battery powered with a variety of mounting options (clipping on to a pannier or a rear rack, for example). There are a wide range of bike lights available; we recommend the Bontrager Flare R or Flare RT, which are available from Trek bike dealers and on the Trek website. Note: if you are renting a bike from Overland this summer, please bring your bike light (your leaders will help you mount it on your rental bike).
- Bungee Cords (3)
These should be 18-24" in length. Bungee cords are included with an Overland bike rental.
- Water Bottle Cages
Two cages, attached to the bike frame. Some smaller-sized bike frames cannot accommodate two cages. If this is the case, you will be able to carry water bottles in your panniers or on your rack. All Overland rental bikes come with two water bottle cages.
- Spare Bike Tube
Spare tube that matches your bike's tire size. All Overland rental bikes come with spare tubes.
- Shoes for Biking
You may ride in running shoes with flat pedals or bring bike touring or mountain biking shoes with bottom treads and "clipless" recessed cleats. The bikes we rent come with flat pedals appropriate for biking in running shoes. If you wish to ride in biking shoes, you will need to bring your own "clipless" pedals. A popular style of clipless shoes and pedals are SPDs. Please do not bring racing shoes since they have hard soles that are uncomfortable to walk in.
Flip flops or Crocs work well.
- 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
- Gallon Sized Ziploc Bags (10)
To organize and waterproof your gear and small items.
- Large Trash Bags (5)
To waterproof your gear.
- Personal Journal or Book (optional)
- Camera, Charger & Extra Batteries (optional)
A digital or disposable camera.
- 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 will update your packing list in April to include currently needed COVID equipment (for example, masks).
- 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).
- A high-visibility outer layer is required at all times while biking. See packing descriptions for more details.
- If you are flying to your trip, pack your sleeping pad and bike shoes in your bike box or checked bag. Take your helmet and sleeping bag with you on the plane as carry-on items, in case your checked luggage fails to arrive on time. Pack all remaining items in your checked duffel bag or in your checked panniers.
- 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.
Please tell me about Overland's COVID policies.
The Overland team is planning, preparing, and eagerly awaiting summer 2021. While we can’t predict what the coming months will bring, we do know how we will face them: optimistically, realistically, and together.
As we plan for the summer, we know that our existing trip structure is ideal:
Small groups (twelve students and two leaders)
Limited contact with the general public
In addition, this summer we will:
Treat our groups as family units / pods
Maintain social distance and wear masks when near the general public
Require a negative PCR test before trip start
Encourage smart air travel practices (for example, wear N95 masks in airports and on board)
We will continue to refine these policies as summer approaches, always with the goal of taking a thoughtful, commonsense approach to maintaining our students’ health and well-being.
Everyone here at Overland is committed to supporting each of our Overland families. Please call on us with any questions or concerns you might have.
Is Overland offering flexibility to those students who are eager to travel abroad?
Yes. We will offer all of our students enrolled on our international trips the option of reserving a backup spot on a U.S. trip.
Is Overland offering any additional flexibility to families this spring in terms of payments?
Yes. We have made all payments fully refundable until Saturday, May 15.
What is the weather like on Vermont?
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, they should be dropped off and picked up in Williamstown, Massachusetts.
How often will my child have access to showers and laundry?
While we have regular access to showers, most students will shower once or twice a week. Groups will do laundry once a week.
What are meals like at Overland? Can Overland accommodate allergies and intolerances?
Meals at Overland
Good food (and plenty of it!), excellent nutrition, and fun are the goals of Overland’s meals. Each group buys, prepares, and eats all of its meals together. Our students, with their leaders’ supervision, prepare all meals. A typical breakfast has cereal, milk, juice, and fruit; most lunches are sandwiches (or wraps) with a variety of fillings, plus chips, and fruit; dinners reflect easily prepared group meals like pasta, burritos, and stir-frys (all of which will typically have a selection of sauces and fillings). At Overland, meals are a group experience, an important way to foster connection with and consideration for other group members.
Allergies & Intolerances
We recognize there are many young people with food allergies or intolerances. We welcome these young people’s interest in joining us, and we ask parents of a prospective Overland student with an allergy/intolerance to please consider the following important information.
Most meals at Overland are prepared in basic kitchens (or outdoors), and groceries are typically purchased from small stores with limited choices. As a result, meals are prepared and served in what may be allergen-contaminated environments, and on many trips allergen-free/gluten-free foods are not readily available. While we cannot guarantee allergen-free meal settings, we will do what is reasonable to provide allergen-free/gluten-free foods on those trips where available.
In all things, our top priority is to help maintain all students’ well-being; to this end, all Overland leaders are trained to recognize and respond to allergic reactions, including administering antihistamines and epinephrine (both are carried in every trip’s first aid kit); leaders carry cell phones, and in some cases, satellite phones, so that should the need arise, emergency personnel can be contacted and their services requested. It is important for all prospective parents to understand that many groups travel in remote areas where emergency services may not be easily or readily accessible.
Our Admissions Process is Collaborative
During our admissions process, we will review all submitted Allergy Questionnaires to understand the applicant’s allergy/intolerance. We will then consider whether or not the applicant’s allergy/intolerance may be reasonably accommodated. If our admissions team has any concerns, they will contact the parent. In this conversation, we will seek to learn more about the allergy/intolerance, and we will discuss the available grocery stores, emergency services, and medical facilities on the applied-for trip. These conversations generally have one of three outcomes:
- The applicant is placed on the applied-for trip if the applicant otherwise qualifies.
- We offer a different trip if the applicant otherwise qualifies.
- We recommend waiting a year and re-applying.
Managing Food Allergies/Intolerances is a Partnership
Our commitment is to the health and well-being of each of our campers. Our goal is to partner with parents and campers—a partnership in which:
- We clearly describe our trips and policies;
- Parents clearly describe their child’s allergies or intolerances and their child’s maturity level and capability to self-manage their allergy or intolerance.
- We work together with parents in a collaborative and interactive process to determine if there are reasonable accommodations that can be made so that otherwise qualified applicants can participate in our trips.
- Students on an Overland trip take an active role in managing their allergies, including reading food labels as needed, eating only those foods with known ingredients, and seeking a leader if a reaction is suspected.
Meals: Vegetarians & Specialized Diets
Every summer there are many vegetarians who join our groups and who enjoy meat-free meals. We are happy to welcome these students as long as they understand they will share in the group’s meals but will simply have the meat portion withheld. For example: sandwiches at lunch with hummus, lettuce, tomato, and cheese (while the rest of the group has sandwiches with sliced turkey or ham); pasta at dinner with a tomato sauce (while the rest of the group has pasta with a meat sauce). We sometimes have requests from applicants with specialized diets—vegans, for example—to provide separate, specialized meals. As much as we’d like to be able to accommodate these applicants, the limitations of our kitchens, the size of available grocery stores, and the importance of group meals make it impractical to provide separate, specialized meals.
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.
How physically challenging are Overland's bike trips?
Overland’s bike trips increase gradually in difficulty–from two weeks on Cape Cod & the Islands to our six-week American Challenge. Many students start on Cape Cod & the Islands (averaging 20 miles of riding per day) or Vermont (averaging 25 miles per day). Nova Scotia & Acadia offers daily rides that are in the 30 to 35 mile range. For students looking for a three week West Coast bike trip, Pacific Coast groups ride 45 miles per day. High school students looking for a physically challenging summer experience can choose from European Challenge, Canadian Rockies & Montana, and American Challenge. These three trips vary in length and location, and on average ride 70, 75, and 85 miles per day, respectively. We’d be happy to talk with you about each trip and the best fit for you: please email us at firstname.lastname@example.org.
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 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.
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
Northward to Canada!
Students going on Vermont should prepare for:
- Full days of outdoor activities led by two caring Overland leaders
- Camping out and cooking meals as a group
- 10 days of biking with an average of 25 miles per day
- A fun, supportive, and wholesome Overland experience
We expect you to arrive to your trip fully prepared for all activities.
Preparing for the Biking
Daily rides on Vermont average 25 miles over varying terrain. The longest day is approximately 40 miles. The route includes rolling hills as well as some significant climbs. The Vermont itinerary also includes one day without riding where you will spend the morning kayaking on Lake Champlain. Groups typically average 6-10 miles per hour while riding. You will take multiple breaks throughout the day — for water, snacks, lunch, etc. — and the goal is to have fun while improving biking skills and overall fitness.
Overland bicycle tours are self-contained — there is no van support. You will carry all of your belongings, plus some group gear and food, on a sturdy rack mounted over the back wheel of your bike. On average, you will carry about 30 pounds of equipment on your bike (not including the weight of the bike).
You should come prepared and recognize that some days will be more challenging and longer than others. Delays occur due to a wide range of variables — weather patterns change and road conditions vary. You, or someone in your group, might get a flat tire or encounter another mechanical issue that could delay your group. On some days your group will arrive at camp in the early afternoon, with plenty of time to explore, play games, or go swimming, while on other days your group will spend more time on the bike.
Our Vermont trip is designed to be a cooperative, non-competitive experience where everyone contributes and helps one another. While there is always a range of physical ability in each group, it's important that you follow our training schedule and that you take the time to gain confidence on a bike — mounting and dismounting, shifting gears, braking and making turns. Enjoy your rides this spring...and we'll see you in Vermont this summer!
- 3 weeks before your trip: Three rides of 4-6 miles each.
- 2 weeks before your trip: Four rides of 6-8 miles each.
- 1 week before your trip: Five rides of 8-10 miles each.
Responsible Riding Practices
In addition to building your fitness and familiarity with bicycling, preparation for Vermont includes increasing your awareness of responsible riding practices. We encourage you to follow the guidelines below when training for your trip and to consult with local bike shops for route and riding advice.
Wear a helmet and closed-toed shoes
Always, no exceptions.
Design a good training loop
To the extent possible, ride on bike paths, bike lanes, and bike routes.
Follow the law
You have the same rights and responsibilities as drivers. Obey traffic signals and stop signs. Ride with traffic; use the rightmost lane headed in the direction you are going.
Make your intentions clear to everyone on the road. Ride in a straight line and don’t swerve between parked cars. Signal turns, and check behind you before turning or changing lanes.
Ride where people can see you and wear a hi-vis top. Ride with your rear light on and flashing. Make eye contact with others and don’t ride on sidewalks. When possible, ride with others.
Watch for turning vehicles and ride outside the door zone of parked cars. Look out for debris, potholes, and other road hazards. Cross railroad tracks at right angles.
Check that your tires are sufficiently inflated, brakes are working, chain runs smoothly, and quick release levers are closed. Carry tools and supplies that are appropriate for your ride.
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.
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Overland offers introductory, hiking, biking, language, writing, service and field studies programs domestically and abroad for students in 4th through 12th grade.