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.


Ride the length of Vermont (and have a blast doing it!).

Vermont in the summerperfect!

Bike along green fields, by red barns, and past white-steepled churches on Vermont’s beautiful back roads.

Biking is fun — really fun — because we do it with a group of new friends. We take our time — it isn’t a race. We stop a lot — for water and snacks and lunch and, yes, for Ben & Jerry’s.

The camping is fun, too, and so are the games and the kayaking. Come to think of it, it’s all fun. That’s the point — two weeks of fun, with new friends and two great Overland leaders.

The kids who come are adventurous, enthusiastic, and friendly. And a lot of them — most of them actually — have never been on a bike trip before. That’s okay. Everyone learns quickly, and our Overland leaders are there to motivate, encourage, and support — every mile of the way from Massachusetts to Canada.

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.