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.

American Challenge

There is nothing else like it.

Read about Our Generous Hosts

From start to finish, the greatest summer of your life.

Cross the country — from the Atlantic to the Pacific — on a trip of unsurpassed adventure, challenge, and accomplishment.

This trip is hard. Really hard. But it’s simple, too. Just wake up every day for six weeks, get on the bike, and head west. It’s no more complicated than that.

Sharing the experience with your group and your Overland leaders makes all the difference. We can promise you this: you have never relied on the support and encouragement, the friendship and fun, of any group of people as much as you will on the American Challenge. That is what makes it so great.

There are markers all along the way of our steady progress toward the Pacific. Reaching the Mississippi. Rolling across the Great Plains. Climbing the Rockies. Marveling at the desert. Riding up and over the San Gabriels and into Los Angeles.

On the last day of the trip, we’ll reach the coast. We’ll sprint across the sand, front wheels in hand, and dive into the crashing waves. Surrounded by trip mates with whom we have shared every day, every mile and every moment of these past six weeks, we’ll scream, yell, shout, and hug. And you’ll know then how hard, how simple, and how wonderful the American Challenge is.

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.