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My Oregon Trail: Trekking from Boston with $200 and a bike

People were friendly when I arrived in Oregon from Boston in 1976. 

“What brought you here?” they’d ask. 

Why We Wrote This

A story focused on

The truly courageous part of doing something, our essayist finds, is to begin it. You cannot persevere if you talk yourself out of it. Once you’ve begun, you need only keep going.

“A bicycle,” I’d say. 

Back then, cash machines and cellphones did not exist. We were accustomed to running out of money and being out of touch. I set out with two male companions, $200 cash, and a shiny new Mastercard. 

None of us had trained. We chafed in cotton shorts. We didn’t wear sunglasses, sunscreen, or helmets. We started on June 1. 

I didn’t worry about anything. That was my mom’s job. I called her collect four times over the six-week trip. I left out worrisome details – the tornado warnings, the 115-degree heat, and the careening coal trucks.

When we reached the Pacific in mid-July, I was brown as a nut and had flossable quadriceps. We looked like Greek gods. There were still donuts for sale, however, and I reassembled my former shape in record time.

What looked like courage in my case was probably just youthful ignorance and groundless optimism. I did learn something about perseverance, though: Once you’re in the saddle, you’re more than halfway there. Then you just keep pedaling.

“Visit, but don’t stay,” the governor of Oregon famously said in the ’70s, and when I arrived from Boston, I figured I’d made it in just under the wire. I didn’t know if I’d be accepted. But people were friendly.

“What brought you here?” they’d ask. Oh. I broke up with my boyfriend, nothing was tying me down, I wanted to shake up my life. All of this was true. That’s not what I said, though.

“A bicycle,” I said. Also true.

Why We Wrote This

A story focused on

The truly courageous part of doing something, our essayist finds, is to begin it. You cannot persevere if you talk yourself out of it. Once you’ve begun, you need only keep going.

People tend to be impressed if you’ve biked across the country. It did take effort, but I had some things going for me. Mainly, I already knew at least a dozen friends who had done it, although most had had the good sense to travel west to east, with the prevailing winds. I was not breaking new ground.

I had no expectation that I’d be backstopped or supported, or that it was even possible. Cash machines and cellphones did not exist, so we were accustomed to running out of money, and our loved ones were accustomed to not being in constant touch with us. We have so much to fall back on now that we’ve grown skittish of failure. We can’t even leave our houses without our phones, and we’ve lost sight of what is truly essential for survival.

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