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Portraits Of Boston: Roaming Around

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“We met a couple of years ago at a gas station in South Carolina. At the time, I was hitchhiking and he was riding trains. We traveled together for a bit and he taught me how to hop freight trains. I don’t travel as much anymore, but he kept doing it and we stayed in touch. A couple of days ago, he was in Boston and stopped by to say ‘hi’.”

“In your experience, what’s the best thing about this lifestyle?”

“For me, it’s the freedom to roam around: you can go anywhere and be in a different place every day. And I’ve made lifelong friends who I first met on the road. Look at us: I’m from western Pennsylvania, in the middle of nowhere, and she is from here.”

“What’s really cool when you get a ride is that you are a stranger and they know they’ll never see you again, so they tell you things they haven’t even told their spouses.

Also, we were just talking about how some days are really bad: You can’t get a ride, so you are stuck in some weird place, and you sleep outside—freezing. Then, the next day, you will be exactly where you want to be: you’ve met awesome people, and you are in a beautiful hotel room and having a huge dinner. The beautiful thing about all of this is that you are just putting yourself out there for chance and fate. Anything can happen. The allure is that you just don’t know. But I’ve never gotten a bad ride, and I’ve never, ever, come across any danger.”


Portraits of Boston is a project of independent photographer Ivan Velinov. He is regularly sharing some of his favorite portraits with WBUR. Visit his website to see the hundreds of portraits he has taken on the streets of Boston.

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