The First Time I Biked Across America

Annalisa van den Bergh
Work From Bike
Published in
4 min readFeb 11, 2018

10 years ago, I was in 10th grade.

I had a habit of staring out the window while my history teacher went off on tangents. I would daydream about how my upcoming summer, during which I would bike from Seattle to New York City with a bunch of strangers, would be like nothing else I had experienced in my young life.

Boy, was I right.

The ceremonial Pacific and Atlantic wheel dips.

If you haven’t already noticed, I’ve always been a sucker for the romanticism of biking across America. For the dipping of the tires in both oceans. For the crushing of the seemingly impossible. For those small towns in the middle of nowhere.

10 years on, that first trip still feels like yesterday.

So much has happened since then yet I can still remember the name of that tiny town in Montana where the laundromat ruined all of our clothes. That cafe in Minnesota that sold square pies. I remember the slew of toys and games we somehow managed to strap to our weighty loads. The times we played frisbee over the Continental Divide and those pitch dark rail trail tunnels in Wisconsin. Every time we went through one, the boys would have a lightsaber battle. I’ll never forget the Michigan postal worker who gave us $50 and the sweet Ontarian family who let us sleep in their treehouse. Oh yeah — and the time a bridge between Michigan and Ontario, Canada was shut down just for us to safely cross it.

From left to right: Amos, Annalisa, Alex, Kate, Kelley, and Matt | Minneapolis, MN

The liberation that comes from taking on such a journey is a feeling that I still have trouble putting into words. Yet it’s all I talk about.

One whole decade has passed. We’ve all grown up but that trip still holds tremendous meaning in each of our lives. It taught us that the simple act of riding a bicycle really, really far does wonders. It ignites utter joy and brings people together. It gives you ridiculous tan lines and stories to tell to your grandchildren.

Our leaders, Matt and Kelley — who we jokingly called mom and dad on the trip — ended up getting married, moving to an island not far from where we started our journey, and becoming parents themselves. And I guess it’s not surprising that many of us have chosen to continue to live a life in motion. Amos is a sailor, Alex is a pilot, and Annalisa’s still riding bikes.

Glacier National Park, MT
Hingham, MT
Wolf Point, MT
Lightsaber battles | Elroy, WI
Reed City, MI
Niagara Falls, NY
Buffalo, NY
Herkimer, NY
Amsterdam, NY
Note the fanny pack strapped to my handlebars | New York, NY
New York, NY

Teen Treks is an organization that gives teenagers the opportunity to go on self-supported bicycle tours. It wouldn’t be an overstatement to say that they changed my life.

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