Weston was born on the outskirts of Detroit, and grew up in Milwaukee. After dropping out of the University of Wisconsin Milwaukee, he took to wandering the country by means of freight trains and hitchhiking. He wanted to gain some understanding of how to live in a meaningful way. Weston took up a camera with the intention of capturing the life he encountered in his travels. After briefly studying photography and film at City College of San Francisco, he went back to the road. A restless spirit, Weston has lived in Madison, WI, Seattle, San Francisco, and New York City.