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.
Cape Cod & the Islands was amazing! We saw breathtaking sights and biked outstanding bike paths.
- Isabella Halkos, Atlanta, Georgia
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. Itinerary may vary by group and is subject to change.
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!
- 4 weeks before your trip: one or two rides of 5 to 8 miles each.
- 3 weeks before your trip: two or three rides of 5 to 10 miles each.
- 2 weeks before your trip: three or four rides of 5 to 12 miles each.
- 1 week before your trip: four or five rides of 5 to 14 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.
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.