American Challenge

There is simply nothing else like it.

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.