Bike rides and beaches, friendships and fun—the best two weeks of your summer.
This was the original Overland trip—and it’s still our most popular. It’s easy to understand why—every day brings great beauty, lots of activities and much to explore. Add gentle (for the most part!) terrain, and you have a wonderful introductory bike trip—two weeks of adventure and exploration.
Over the years, the trip has changed little: the routes (always the best we can find); the activities (swimming and games); the kids (almost all first-timers on a bike trip); the leaders (super responsible and a lot of fun, too). These are some of the reasons why the trip is so popular (12 groups every summer!).
Since our very first trip in the mid-1980’s Cape Cod & the Islands has offered enthusiastic students the chance to explore this beautiful part of New England in a supportive, wholesome group with caring Overland leaders. It’s a simple formula—and it’s worked for over 30 years.
I can't thank you enough for this amazing experience for my daughter. It couldn't have been any better!
- Courtney Goldstein, Briarcliff Manor, New York
Trip Start and First Orientation Rides
We will meet in Williamstown, Massachusetts, and spend the afternoon adjusting to our bikes, packing our panniers, learning riding etiquette and getting to know one another. With three or four groups on the Cape at once, we will run at least three different itineraries. Typically one group will start on Martha’s Vineyard then travel to Nantucket and finish in Provincetown; a second group will do that same itinerary in reverse; a third group will start on Nantucket, travel to Martha’s Vineyard and finish in Provincetown.
In the morning, we will drive to Cape Cod in a 15-passenger van with our bikes and gear in tow. On the Cape, we’ll start our self-supported bicycle tour. The Cape offers beautiful beaches, quiet back roads and a rail trail. Averaging 20 miles per day, we’ll bike through forests, past marshes and beaches and visit Hyannis, Wellfleet and Truro. The terrain on the Cape is generally hilly and rolling with some flat sections.
Nantucket and Martha’s Vineyard
On Nantucket and Martha’s Vineyard, we will ride on bike paths to classic seaports, charming towns and long stretches of white sand beaches—perfect for an afternoon of swimming and games. The terrain on the islands is generally rolling, and there is a mixture of quiet roads and bike paths. On Martha’s Vineyard, we’ll stay at a campground a short bike ride from the beach. On Nantucket, we’ll stay at a hostel right on Surfside Beach.
Whale Watch off Provincetown
In Provincetown, we’ll board a whale-watching vessel to explore an area off the tip of the Cape where these giant mammals feed. If we are lucky, we may see whales and other sea life.
At trip end, we’ll return to Williamstown by van and enjoy dinner as a group. We will celebrate two weeks of biking, beaches and adventure on Cape Cod & the Islands.
10 nights of frontcountry camping. Campground facilities may vary; all include flush toilets and hot water, most have showers and laundry.
2 nights in a hostel in Nantucket. The hostel has dormitory style accommodations with separate rooms for boys and girls. Some groups may stay additional nights in a hostel depending on the section and itinerary.
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).
- 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 start, 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. You can tape or strap your panniers together to check them as one piece of luggage; see luggage description for more details.
- There are no reimbursements for lost, damaged or stolen items.
- Please wear the navy Overland shirt that you will receive from the Overland office to your trip start location.
- 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 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.
- Synthetic High-Visibility T-Shirts (3) & Vest (1)
A high-visibility outer layer, preferably a solid color, 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. Please visit the Overland Store if you need to purchase these items. High-visibility bike jerseys are acceptable but not necessary.
- Shorts for Biking (3)
Synthetic material recommended (some students bring padded, spandex bike shorts but they are not required).
- Shorts (1)
Comfortable shorts to wear around camp.
- Synthetic T-Shirt (1)
Short-sleeve T-shirt or tank top.
- Long-Sleeve T-Shirt (1)
Lightweight for sun protection.
- Underwear (5)
- Athletic Socks (pair) (4)
- Synthetic Long Underwear Top & Bottom (1)
- Wool and/or Synthetic Socks (1)
- Swimsuit (1)
- Pajamas (optional)
Students sometimes prefer to sleep in shorts and a T-shirt instead of bringing pajamas.
- Fleece Jacket or Pullover (1)
Medium to heavyweight and reasonably compact.
- Waterproof Raincoat (1)
Waterproof material required (not just water resistant). Choose high-visibility if available (a high-visibility outer layer is required at all times while riding; if your raincoat is not hi-vis then you'll have to wear a hi-vis vest over your raincoat when riding). Raincoats 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.
- 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
Full- or ¾-length compact sleeping pad. We recommend closed cell foam that is thin and firm (e.g., RidgeRest) or self-inflating (e.g., Therm-a-Rest).
- 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 & Extra Batteries
- 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) works well. If you bring a backpack, it must be high-visibility and it 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 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. Please see the Right Bicycle for Your Overland Trip for more information about acceptable bikes and traveling with your bike.
- 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 when riding in low light conditions. The light should be battery powered with a variety of mounting options (clipping on to a pannier or a rear rack, for example). The Portland Design Works Radbot 1000 and the Planet Bike LED Superflash turbo are two examples of bike taillights. Even if you are renting your bike from Overland this summer you will need to supply your own light for your bike.
- Water Bottle 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 strap additional water bottles to your rack with your other gear. All Overland rental bikes come with two water bottle cages.
- Spare Bike Tubes (1)
Spare tube that matches your bike's tire size. All Overland rental bikes come with spare tubes.
- Shoes for Biking (pair)
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.
- Sandals (pair)
Flip flops or Crocs work well
- Photo Identification
A current school or other kind of photo identification (if you have one).
- Synthetic Camping Towel
A medium-size synthetic camping towel (synthetic camping towels dry much faster than regular towels).
- Gallon Sized Ziploc Bags (10)
To organize and waterproof your gear and small items.
- Large Trash Bags (5)
To waterproof your gear.
All items should be travel size (if necessary, you will be able to restock during the trip).
Polarized sunglasses that wrap around to protect from glare are ideal.
- Sunscreen (SPF 15+) & Chapstick (with SPF protection)
- Insect Repellent
- Personal Journal or Book (optional)
- 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).
- Spending Money
$30 per week in cash or a debit/ATM card.
- Health Insurance Card
Please bring an original or copy of your health insurance card.
- What is the weather like on Cape Cod & the Islands?
The weather on Cape Cod & the Islands 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.
- 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). 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.
- 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.
- 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. Teamwork and Shared Responsibilities.
2. Independence and Self-Reliance.
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.
Bike, swim and explore Cape Cod, Nantucket and Martha’s Vineyard.
Students going on Cape Cod & the Islands should prepare for:
- 10 days of biking with an average of 20 miles per 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 Biking
Daily rides on Cape Cod & the Islands average 20 miles over varying terrain. The longest day is approximately 30 miles (the exact mileage may vary by group). The terrain will be mostly flat, but the route does include a few substantial hills.
Overland bicycle tours are self-contained—there is no van support. You will move camp every two to three days. On these days, 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. You will hang panniers (these are saddlebags, pronounced “pan-yers”) off the rack and attach gear like your sleeping bag and sleeping pad to the top of the rack using bungee cords. On average, you will carry between 30 and 40 pounds of equipment on your bike (not including the weight of the bike). On other days, you will take day rides as a group—to a beach, lighthouse or into town—with little to no weight on your bike.
Cape Cod & the Islands is designed to be a cooperative, non-competitive group activity where everyone contributes and helps one another. While there is always a range of physical ability and fitness 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. We expect you to prepare adequately so you can keep up physically and participate in all of your group’s activities.
Responsible Riding Practices
In addition to building your fitness and familiarity with bicycling, preparation for Cape Cod & the Islands includes increasing your awareness of responsible riding practices. Your Overland leaders will review safety practices and reinforce responsible riding at trip start and each day of riding.
The following guidelines have been developed by the League of American Bicyclists to help manage the risks associated with biking on roads; however, managing risks does not eliminate them. We encourage you to follow these guidelines when training for your trip, and we also encourage you to consult with local bike shops for route and riding advice.
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 well before turning or changing lanes.
Ride where people can see you and wear bright clothing. Use a front white light, red rear light and reflectors when visibility is poor. Make eye contact with others and don’t ride on sidewalks. When possible, ride with others; do not ride alone.
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. Wear a helmet.
Adapted from “Rules of the Road,” http://www.bikeleague.org/.
- 4 weeks before your trip: two rides of 5 to 8 miles each.
- 3 weeks before your trip: at least two rides. One of 5 to 8 miles and a second ride of about 15 miles.
- 2 weeks before your trip: at least two rides of about 15 miles each.
- 1 week before your trip: at least two rides of about 15 miles each. A good goal to work towards is being able to complete your long rides without too many prolonged breaks.
Groups typically average between 6 and 10 miles per hour while riding (although pace varies by group). You will take multiple breaks throughout the day—for water, snacks, lunch, to adjust panniers, etc.
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.
All trips have a range of challenges. You should come prepared and recognize that some days will be more difficult, more challenging and longer—both in terms of miles and hours on the bike—than others. Delays occur due to a wide range of variables beyond the control of you, your group or your leaders. Weather patterns change and road conditions vary. You, or someone in your group, might get a flat tire or encounter another issue that could delay your group. On some days your group will arrive in to 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.
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 program.