Cape Cod & the Islands

For anyone looking for a great place to start, there's no better teen summer bike trip than Overland's Cape Cod & the Islands. Explore the Cape, Nantucket and Martha's Vineyard. Ride to beautiful beaches and picturesque towns. Look for whales on a day trip out of Provincetown. Enjoy two weeks of biking and beaches, friendship and fun.

Overview Details Itinerary What to Pack FAQs Before You Go


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 lots to see and lots to do. 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-1980s, Cape Cod & the Islands has offered enthusiastic, adventurous students the chance to explore this beautiful part of New England in a supportive, wholesome, and fun group with caring Overland leaders. It’s a simple formula—and it’s worked for 35 years.

Good Things to Know. The group is always small—no more than twelve students—and we always have carefully chosen and thoroughly prepared leaders. The itinerary is crafted to provide just the right mix of activities (biking and beaches, fun and games): the goal is to have every student love their Overland experience. The biking is designed thoughtfully: leaders at the front and rear, helmets, hi-vis shirts, and rides on the best available roads, routes, and paths. The routes and distances are chosen to accommodate first-timers with shorter mileages and gentler grades than our other bike trips. The camping is in private campgrounds, all of which offer full facilities, including hot showers. There are a handful of nights in youth hostels which provide dormitory accommodations, bathrooms, showers, and a full kitchen. Meals are wholesome, nutritious, and varied… and they’re fun group projects with input from everyone and lots of guidance from the leaders. Getting to and from the trip is a breeze: we start and finish in Williamstown, Massachusetts (Overland’s home base), which is an easy drive from most points in the Northeast, and there are plenty of flights (on United, American, and Southwest) into the nearby Albany, New York, airport (we provide supervision on arrival and departure—and a shuttle to Williamstown—so that travel days go smoothly).

Questions? Contact us!

Cape Cod & the Islands was amazing! We saw breathtaking sights and biked outstanding bike paths.

- Isabella Halkos, Atlanta, Georgia

Two weeks of fun & friends on the Cape & Islands.

Trip Start & 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; and a third group will start on Nantucket, travel to Martha’s Vineyard and finish in Provincetown.

Cape Cod

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 & 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.

Trip End

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.

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

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. Choose high-visibility if available.

General Gear

  • 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).
  • Headlamp
  • Water Bottle
    A 24-ounce bike bottle is ideal (on arrival you will receive a second bottle from us).

Bike Gear

  • 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.
  • 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.


  • 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.
  • Sandals
    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
  • Sunglasses
  • 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.

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).
  • 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.

  • What is the weather like on Cape Cod & the Islands?

    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?

    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 trip. If your child is not flying to the start of the trip, he or she should be dropped off and picked up in Williamstown, Massachusetts.

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

    We have regular access (almost daily) to showers, but as with any camping trip, showering tends to not be a daily activity. Groups will do laundry once a week.

  • Please tell me about safety at Overland.

    Safety and risk management are at the forefront of our decision-making–from trip planning to leader training to supporting our groups in the field. We cannot guarantee absolute safety–no program can. All recreational activities include inherent risks. Therefore, we strive to manage the risks that we can, knowing we cannot eliminate them. We work hard to recruit, train and support our trip leaders so they can create the kind of trips that have made us successful for over 30 years. Please click here to read more about our approach to risk management and our accreditation by the American Camp Association.

  • Does my child need to have previous experience?

    While no previous experience is required, we have high expectations of our students. We expect your child–with your help–to select a trip that is appropriate for their interests and abilities. You should spend some time familiarizing yourself with the details of the specific trip and help your child understand what to expect. We also expect our students to prepare ahead of time: to review the packing list, gather clothing and gear and complete whatever training the trip requires (for recommended training please see the Before You Go tab). Once the trip begins, your child should be ready–and excited–to contribute to a wholesome and enthusiastic group 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.

Bike, swim and explore Cape Cod, Nantucket and Martha’s Vineyard.

Students going on Cape Cod & the Islands 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 20 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 Cape Cod & the Islands average 20 miles over varying terrain. The longest day is approximately 30 miles. The terrain will be mostly flat to rolling with a few substantial hills. Cape Cod & the Islands groups typically average 8-10 miles per hour while riding. There are always lots of breaks—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 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. On average, you will carry 30 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.

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.

Cape Cod & the Islands 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 on the Cape and Islands this summer!

Pre-trip Training:

  • 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 Cape Cod & the Islands 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.

Always, no exceptions.

To the extent possible, ride on bike paths, bike lanes, and bike routes.

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.