We Welcome Your Application to Join Us!

We build each of our groups with care, keeping the groups small (no more than twelve students), and paying close attention to age, grade, gender, and the mix of hometowns and schools. Our goal is to put together great groups — groups where nice kids thrive in a supportive, wholesome, and caring environment. Please note: availability as shown is based on students traveling without a friend; if your child is interested in traveling with a friend, please call our office for availability.

Important Information about Availability


This departure of this trip has good availability. Apply as soon as possible since availability changes quickly.


This departure of this trip has limited availability. Apply as soon as possible, and on receipt of your application, if space is still available, we’ll confirm a spot for you. If all of the spots are taken, we’ll call you to discuss options.


This departure of this trip is currently full — please call us to discuss options.

How to Apply

Apply online using a credit card for the $795 deposit (your card will not be charged until we confirm a spot for you). Applications are reviewed in the order in which they are received (we do not hold spots over the phone).

When to Apply

The flow of applications starts in July and peaks in January/February. Some groups fill by the December holidays, and others will have space into the late spring. Our advice? Apply as soon as possible — it only takes a few minutes — and we’ll get to work right away to find a great spot for you.


Call (413.458.9672) or email (info@overlandsummers.com). We look forward to hearing from you.

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. 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

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