Cape Cod & the Islands

Overview

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 explore beautiful beaches and picturesque towns on back roads and bike paths. Cape Cod & the Islands offers challenge, camaraderie, biking, 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 back roads 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 the islands while making friends and having fun. A whale watch off Provincetown rounds out two weeks of biking, beaches and fun on Cape Cod & the Islands.

“Alex grew as an individual, took risks and gained confidence in becoming independent." Lisa Calvert, Sammamish, Washington

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 2010.

Call us (800.458.0588) to check on current availability.

Challenge Level

2 (1-10, 1 is easiest)

Start and End Location

Cape Cod & the Islands starts in Williamstown, Massachusetts. For students who drive to the start of the trip, 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.

Dates and Fees

2 Weeks

Sunday, June 27 to Friday, July 9
Sunday, July 11 to Friday, July 23
Sunday, July 25 to Friday, August 6

$2795

“One of the best parts was having dessert circle on the beach under the stars.” Rose Hedreen, Williamstown, Massachusetts

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.

“We are tough critics, but we were very impressed by the professionalism and thoughtfulness of every aspect of Overland and the Cape Cod & the Islands.” Doug Elmendorf and Karen Dynan, Bethesda, Maryland

Trip Details

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 4). 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.

“My leaders were awesome!” Alex Calvert, Sammamish, Washington

Photos

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Prepare & Pack

Cape Cod & the Islands

Preparing for the Biking

Training ahead of time is essential to your success on an Overland bike trip. Training will enable you to enjoy your trip and to ride safely this summer. The most important part of training is gaining confidence on your bike by riding regularly. Please take two 30- to 45-minute rides every week for four weeks before the start of your trip. Your health and safety this summer depend on this. Before your trip you should be comfortable getting on and off your bike, shifting gears, braking, and making turns; and you should be able to ride 10 miles with ease. A good goal to work towards is being able to ride 15 miles in one ride, although frequent shorter rides (5-8 miles) are a great way to become a confident and safe rider.

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.

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.

Packing for Your Trip

Our packing list is designed to keep you safe and comfortable while biking and camping this summer. Keep in mind, however, that there are a wide range of products available in terms of clothing and equipment. Overland programs are relatively short and although you want your clothing and equipment to be durable, this does not mean it has to be top of the line. Often times more basic and less expensive options perform just as well. Some of our favorite brands in terms of quality of product for a reasonable price include REI, EMS and L.L.Bean.

Label the following items with your name, address and phone number.  Bring only what you need and pack everything in your panniers, or in a duffel bag if you are renting panniers from Overland. You can tape or strap your panniers together to check them as one piece of luggage. Please take your helmet, sleeping bag and pad with you on the plane as carry-on items in case your checked luggage fails to arrive on time.

Please bring only the clothes listed below. Do not wear an extra set of clothes for the flight. By layering you will stay cool on warm days, dry on rainy days and warm on cool nights. You will have the chance to do laundry periodically.

Clothing

• Fleece Jacket or Pullover & Long Fleece Pants
  Please don't bring jeans or sweatpants. They are heavy, bulky and will not keep you warm if wet.


• Waterproof, Breathable Rain Jacket
  Your rain gear must be waterproof (not just water and/or wind resistant). GoreTex is one of the better-known waterproof, breathable fabrics, but there are many of these fabrics to choose from. Ponchos are not acceptable as they are difficult to ride in and don't provide the same protection that rain jackets do.


• Shorts To Bike In
  Three pairs. Synthetic recommended (some students bring padded, spandex bike shorts but they are not required).


• Around Camp Shorts
  One pair. Athletic shorts work well around camp as they are comfortable to wear, light and compressible to pack.


• T-Shirts
  Three. Synthetic or cotton.


• Underwear
  Five.


• Socks
  Five pairs; at least one warm, synthetic pair for inclement weather and around camp.


• Pajamas
  One pair only. Pajamas aren't required as many students sleep in shorts and a t-shirt.


• Bathing Suit
  One only.


• Sport Sandals
  With a heel strap for swimming and around camp. Flip-flops are also okay if you do not have sport sandals.

Biking & Camping Equipment

• Helmet
  Carry on the plane with you.


• Water Bottles
  Two. 24 oz bike bottles are the best size to aim for, but smaller sizes are okay if that is what you have. A hydration system (e.g., CamelBak) is not necessary, but if you have one and want to bring it, that's great.


• Shoes For Biking
  Any comfortable running shoes, all-terrain shoes or sneakers are fine.


• Sleeping Bag
  Warm to 30 degrees or less. Lightweight and compact (when stuffed in a compression stuff-sack it should be no larger than 12" x 20"). Synthetic or down is acceptable. Carry on the plane with you.


• Sleeping Pad
  Compact and either 3/4 or full length. Closed cell foam (thin and firm—e.g., RidgeRest) or self-inflating (e.g., Therm-a-Rest) is acceptable. Carry on the plane with you.


• 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 Rubbermaid dish (or similar) and regular utensils are fine.


• Headlamp
  Small and lightweight. This comes in very handy in camp when it's dark and you're using both hands.

The following items are available for rent from Overland.
Please see the Bicycle & Pannier Rental form.

• Bicycle & Rear Rack
  Please see The Right Bicycle For Your Overland Trip in the Admissions Materials. Please note: If you plan to do the American Challenge or European Challenge in the future, and you are buying a new bike now, a touring bike is required for these challenge trips. If you need assistance in choosing a bicycle, please contact Ashley Ransom at ashley@overlandprograms.com.


• Water Bottle Cages
  Two. Attached to the bike frame. Note: Some smaller size bike frames can not accommodate two cages. That's okay, as you'll be able to strap additional water bottles to your rack with your other gear.


• Panniers & Two Bungee Cords
  Panniers are saddlebags sold in pairs that attach to either side of your rear rack. For our trips you will want large panniers, 2500-3500 cubic inches total, designed for 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. Consider compressibility of clothing while packing for your Overland bicycle tour.


• Spare Bike Tube
  One spare tube that matches your bike's tire size.

Miscellaneous Gear

• Towel
  Medium size cotton or synthetic. A beach towel is fine.


• Plastic Bags
  Ten large ziplocks and five tall kitchen trash bags. The trash bags will be used to line your panniers and to wrap your sleeping bag and pad in. The ziplocks will be used to organize and waterproof the rest of your gear.


• Toiletries
  All travel size (in a plastic bag). If necessary, you will be able to restock en route.


• Sunglasses, Sunscreen (SPF 15+), Chapstick (with SPF protection) & Insect Repellent


• Paperback Book and/or Journal
  Optional. Your group will collectively keep a group journal and you'll receive a copy of the journal after your trip. If you would like to keep your own journal though, you should bring one.


• Camera/Batteries/Memory Card
  Optional.  Interested in seeing your photographs or videos on Overland's website next year?  Bring a camera with lots of pixels (10 or more) and lots of memory (4GB or more).  Buying a new camera?  One of our favorites is the Canon PowerShot SD960 IS digital camera. 


• Spending Money
  $50/week for souvenirs, gifts and necessities (like more sunscreen if you run out or envelopes to mail letters). If you are flying home at the end of your trip, please bring additional money to set aside to pay the airline bike fee for your return flight.

Note: Please do not bring any type of knife or multi-tool (e.g., Swiss Army Knife, Leatherman).

We do not permit personal electronics on our programs (e.g., cellphones and iPods). We do, however, allow students who fly to their program to carry a cell phone while traveling; on arrival, Overland's leaders will collect all cell phones for the duration of the program and return them for flights home. Perhaps, a better option would be to bring a pre-paid phone card so that the leaders do not have to carry cell phones for the duration of the program.

Bringing A Bicycle On The Plane

If you are flying to the start of your trip, you will need to box your bike prior to your flight so that you can check the boxed bike as a piece of luggage. Most airlines charge about $100 to $175 one-way to check a bike. Please let your airline know that you will be bringing a bike, as many small planes cannot accommodate bike boxes. Please bring and set aside money to pay the bike fee for your return flight.

To box your bike, bring the bike to a bike shop where a mechanic will break it down and box it for about $40 to $50. Please make sure the mechanic leaves the cables attached and protected and does not remove the rear derailleur. For instructions on how to box your bike yourself, click here.

Admissions

Below are individual PDFs of the Admissions Materials for Cape Cod & the Islands.

Admissions Materials 2010

Bicycle & Pannier Rental 2010

Bicycle Report 2010

The Right Bicycle For Your Overland Trip 2010

Flight & Travel Information 2010

Program Start & End Information 2010

Apply

We welcome your interest in joining Overland this summer!

To apply, please complete and sign the application on page 47 of the Overland catalog or download an application. (You will need Adobe Acrobat Reader to download the application).

Please refer to page 46 of our catalog for important information you should know before signing the application.

Send your application and $795 deposit to:

Overland
P.O. Box 31
Williamstown, MA 01267

For overnight mail via UPS or FedEx, please use our street address:

Overland
63 Spring Street
Williamstown, MA 01267

Sorry, we are unable to accept applications by fax, and we do not take credit cards. Applications are reviewed in the order in which they arrive at our office and we cannot hold spots over the phone.

To learn about our admissions process, please click here.