Weston was born on the outskirts of Detroit and grew up in Milwaukee. After dropping out of the University of Wisconsin, he wanted to live in a more meaningful way and began exploring the country by means of freight trains and hitchhiking. Weston took up a camera to capture his experiences while traveling. He briefly studied photography and film at City College of San Francisco before returning to the road. A restless spirit, Weston has lived in Madison, Seattle, San Francisco, Oakland, New York City, and Missoula.