The Freewheelin' Bob Dylan album cover features a photograph of a 21 year old Bob Dylan and his girlfriend at the time, Suze Rotolo (an artist who teaches at the Parsons School of Design). History will tell you Rotolo inspired the songs "Don't Think Twice, It's Alright" and "Boots of Spanish Leather." It will also tell you that Dylan wanted to (add a girl and) recreate this shot of James Dean.
The photograph was taken in February 1963 by Don Hunstein. Dylan lived a short ways away at 161 West 4th Street at the time. The cover of this album is often thought to be shot on West 4th Street between 6th and 7th, outside of his apartment. This is not true. The actual street is a one block side street connecting West 4th and Bleeker, called Jones Street. If you see outtakes from this photo shoot you'll see more of the area, in which a building with the number 9 and a decorative diamond shape is visible (and still there today). The fire escapes have since been replaced, but other than that you'll be able to recreate this album cover rather well, on a snowy day.