Overview
Cape Cod & the Islands
for 7th-9th graders
This classic tour of Cape Cod, Nantucket and Martha’s Vineyard is always one of Overland’s most popular trips, and for good reason. Daily rides with a small, spirited group (no more than 12 students or fewer than 2 leaders) explore beautiful beaches and picturesque towns on backroads and bike paths. Cape Cod & the Islands offers challenge and camaraderie, biking and beaches and whale watching off Provincetown.
We’ll start in Williamstown, Massachusetts with a short orientation and a practice ride before we travel by van to the Cape. On the Cape, quiet backroads and beautiful beaches await us. We’ll ride through Hyannis, Brewster and Wellfleet on bike paths and scenic roads that take us through forests, by marshes and past beaches. The terrain is forgiving, allowing us to build skills and fitness as we go. In Truro, we’ll face some challenging hills as we bike through an area of big sand dunes with beautiful views of Cape Cod Bay to the west and the Atlantic Ocean to the east. On Nantucket and Martha’s Vineyard, bike paths take us to classic seaports, charming towns and long stretches of white sand—perfect for an afternoon of swimming and games.
Our daily rides average 20 miles and are a great way to discover the beauty of the Cape and Islands while making friends and having fun. An exciting whale watch off Provincetown rounds out two weeks of biking, beaches and fun on Cape Cod & the Islands--a life experience with value and resonance that extends far beyond the boundaries of a single summer.
HIGHLIGHTS
- Ride quiet bike paths on the Cape
- Swim at Martha’s Vineyard’s South Beach
- Explore Nantucket by bicycle
- See whales off Provincetown
GRADE
For students who will finish grades 7-9 in June 2008. We plan on 2 groups at each departure with 7th & 8th graders and 2 groups at each departure with 8th & 9th graders. Call us (800.458.0588) to check on current availability.
CHALLENGE LEVEL
2 (1-10, 1 is easiest)
START & END LOCATION
Starts and ends in Williamstown, Massachusetts
2008 DATES & FEES
2 Weeks
Sunday, June 22 to Friday, July 4
Sunday, July 6 to Friday, July 18
Sunday, July 20 to Friday, August 1
$2695 (airfare not included)
APPLY TODAY
Most groups fill in January & February. To download an application, click here.
“I had fun making new friends, camping, exploring new beaches and riding on beautiful bike paths.” Jenna Ioffredo, Chatham, New Jersey
Itinerary
At The Start Of The Trip
Cape Cod & the Islands starts in Williamstown, Massachusetts. For those who fly, we'll meet at Albany, New York International Airport; for those who are dropped off, we'll gather in Williamstown on the Williams College campus.
Orientation & First Ride
During the first days of the trip, we'll focus on group building and safe riding. We’ll show you how to set up your tent, how to pack your bicycle and how to ride safely. At the same time you’ll have the opportunity to get to know your trip mates and your two trip leaders (always a male and a female). Most Cape groups have 12 students—never any more—and there are usually 4 or 5 boys and 7 or 8 girls.
Traveling To The Cape By Van
Groups will travel to the Cape the morning after they arrive. We’ll load up a 15-passenger van and a large trailer with all of our bikes and gear and van to the Cape (a four-hour drive). Once we arrive on the Cape, the van will return to Williamstown and we'll start our self-supported bicycle tour. With three or four groups on the Cape at once, there will be at least three different itineraries; typically one group will start on Martha’s Vineyard and then travel to Nantucket and finish their ride 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 addition to beautiful beaches, the Cape offers quiet backroads and a terrific rail trail. We’ll ride through forests, by marshes and past beaches and visit Hyannis, Wellfleet and Truro. The terrain on the Cape is generally rolling—there are some flat sections (the rail trail) and there are some hilly sections (Wellfleet to Truro). Most nights are spent in comfortable campgrounds on the Cape (with hot showers and fully equipped bathrooms) and a few nights are spent in a youth hostel on Nantucket (with dormitories, fully equipped bathrooms and a shared kitchen).
Nantucket & Martha’s Vineyard
On Nantucket and Martha’s Vineyard, bike paths take us to classic seaports, charming towns and long stretches of white sand—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—a favorite with Overland groups. On Nantucket we'll stay at one of the world’s most beautifully sited youth hostels right on Surfside Beach!
Whale Watch Off Provincetown
In Provincetown we’ll board a whale-watching vessel for a three-hour excursion, exploring an area off the tip of the Cape where these giant mammals feed. Most groups are lucky enough to catch a glimpse of these magnificent creatures.
Trip End In Williamstown
At trip end, we’ll return to Williamstown to enjoy a final dinner as a group, rounding out two weeks of biking, beaches and fun on Cape Cod & the Islands!
Supervision & Safety
On an
We set high expectations for each student’s behavior—we expect respect and consideration for others, a positive attitude, and an eagerness to help make the trip a success in every way possible.
In every decision we make, safety comes first. We plan our trips carefully choosing bike paths and bike routes wherever possible, and where they are not available, choosing the best available roads. We ride with care, with a leader at the front and a leader at the rear. We only ride during the day; we always wear helmets, and we attach an orange safety flag to every bike. Since our first trips in 1985 our safety record has been superlative.
For nearly 25 years our caring and competent leaders, our 24/7 supervision, our high expectations, and our commonsense approach to safety have made Overland the number one choice for summer bicycle trips.
Overland Leaders
In a world where strong leadership skills make the difference between the average and the exceptional, Overland recruits and trains only the best to be our leaders. Not only do these remarkable people capably lead our groups, they also offer our students the kind of role modeling for which Overland has long been recognized. Bright, charismatic and accomplished, our leaders ensure the safety and well-being of every Overland student, and then they provide much, much more, inspiring our students to reach for their potential in every way.
You won’t find a more dynamic and talented group of people than Overland’s leaders. Most Overland leaders have played varsity sports and many have captained their teams; they have served as student government officers, volunteered as peer counselors and directed campus organizations. They are high achievers who come to Overland with a lifetime of leadership experience—but just as importantly, they are warm, wonderful people who are eager to work with Overland’s students.
Overland’s leaders prepare carefully for the summer. We know of no other program that requires certification in First Aid, CPR and lifesaving—every Overland leader has all of these plus our own 10-day training program that focuses on safety, supervision and leadership. All of our efforts prepare Overland’s caring and committed leaders to create safe, supportive and valuable programs where each of our students can flourish.
Meet some of our spectacular returning leaders.
Trip Difficulty
Cape Cod & the Islands is rated 2 on a scale of 1-10 (1 is easiest). The length of the rides and the difficulty of the terrain are a bit less demanding than Vermont (Level 3). Our daily rides average 20 miles and are a great way to discover the beauty of the Cape and Islands while making friends and having fun.
Most Cape Cod & the Islands participants are first-timers on a trip like this—so few, if any, students come with prior experience. There is always a range of physical ability and fitness in each group. As long as you are motivated and reasonably fit, you will keep up just fine because the trip is designed to be a cooperative, non-competitive group activity where everyone contributes and helps one another.
Fully Self-Contained Bicycle Trips
Overland bicycle tours are self-contained—meaning there is no van support. You will carry all of your belongings, plus some group gear, 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.
“Nikki loved her trip! She came home happy and confident. She made new friends—her goal for the trip was to be more outgoing, less quiet around new people. Nikki prepared for the trip and found it to be nice that she was more than ready for the physical activity. The trip seemed very well-organized and age appropriate.” Traci Grigg, Washington, D.C.
How We Put Our Groups Together
We have a number of important criteria for every group:
Group Size: Every
Gender:
Friends: We allow two pairs of friends in a group (we never allow three or more friends to travel together). With a maximum of two pairs of friends there will always be space available for at least eight students to come on their own without a friend. Furthermore, if we enroll two pairs of friends in a group and both pairs are of one gender, we generally try to: (1) enroll three or four more students of that gender in that group, or (2) close the group to additional students of that gender.
Leader Comments
To give you an idea of what this trip is like on a daily basis, here are some notes taken by Overland leaders on a recent Cape Cod & the Islands trip…
“We left the Martha’s Vineyard Family Campground after breakfast (we had juice, cereal, bananas and bagels) and rode to Edgartown along the bike path. It’s an easy ride and the bike path is nice. The ride to Edgartown is about eight miles from the campground. We had a picnic lunch on the museum’s lawn in Edgartown (we bought our lunch groceries at the Stop & Shop in Edgartown: cold cuts, cheese, chips and pears). After lunch we rode to South Beach for the afternoon. The ride to South Beach is easy and is about 5 miles; we followed the Katama Road beach bike route signs to get there. South Beach is a nice beach, with good waves and a medium undertow; it wasn’t too crowded and we spent most of the afternoon there swimming and relaxing on the beach. At the end of the day we returned to Edgartown; stopped at the Stop & Shop for groceries for dinner (we picked up fixings for tacos: taco shells, ground beef, beans—for the non-meat eaters—lettuce, tomatoes, salsa, and cookies for dessert). Once we got back to the campground we took showers and prepared dinner. It was a tiring day with lots of activity so we had dessert circle at about 9:00 and everyone was asleep in their tents before 10:00. It was a great day!”
“JJ rated this trip a '10 out of 10'. He is not drawn to hyperbole so this is a real endorsement of his view of the trip.” William Nance, Bloomfield Hills, Michigan
Trip Details
Getting To & From The Trip
Cape Cod & the Islands starts in Williamstown, Massachusetts. For students who drive to the start of the trip (Williamstown is 3 hours north of New York City and 3 hours west of Boston), we’ll meet on the Williams College campus. Students who fly to the trip start should fly into the Albany, New York airport where Overland staff will be on hand to meet you, help you collect your baggage and transport you by 15-passenger van the 42 miles to Williamstown.
At the end of the trip students will be shuttled back to Williamstown. Students can either fly home from Albany, New York airport or be picked up in Williamstown. Overland staff will be on hand to assist all students with flights or pick-ups.
Equipment
Please see the Preparing & Packing page for a complete packing list. Note that the main pieces of equipment needed for this trip are: a bike (available for rent from Overland), a helmet, panniers (saddlebags—available for rent from Overland), a sleeping bag and a sleeping pad.
The Bicycle
You will need a good quality bicycle for this trip. You can either bring your own or rent a bicycle from Overland. Complete information to help guide you in the selection of an appropriate bicycle or arrange for an Overland rental is available in the Choosing the Right Bicycle and the Bicycle & Pannier Rental Form in the Enrollment Forms.
Renting a Bicycle and Panniers From Overland
You may choose to rent a bicycle and/or panniers from Overland to use during your trip. Please see the Bicycle & Pannier Rental Form for more information (click above on Enrollment Forms).
Additional Costs
Transportation to and from program start and end locations, spending money and personal gear are not included in the program fee. Overland provides group gear including tents and stoves; students provide all personal equipment (e.g., bicycles, panniers, sleeping bags).
“A safe, adventurous trip with enthusiastic and caring leaders, geared to young teens—perfect!” Alice Hadley, Williamstown, Massachusetts


