Cape Cod & the Islands

There's no better bike trip than Overland's Cape Cod & the Islands.

Bike rides and beaches, friendships and fun — the best two weeks of your summer.

Explore Cape Cod, Nantucket, and Martha’s Vineyard. Ride to beautiful beaches and picturesque towns. Look for whales on a day trip out of Provincetown.

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 12 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).

Have a question about availability?

Contact Us or call: (413) 458-9672

Explore Similar Trips


Explore Other Trips

Overland offers introductory, hiking, biking, language, writing, service and field studies programs domestically and abroad for students in 4th through 12th grade.