Highway 61 is a real road that runs from Minnesota to New Orleans. Dylan said in his book Chronicles: "Highway 61 begins about where I came from, Duluth, to be exact." He added, "I always felt like I'd started on it, always had been on it, and could go anywhere from it."
Highway 61 runs from Dylan's hometown of Duluth, Minnesota, all the way to New Orleans. It is notable for being a major transit point for southerners heading north to cities such as Chicago, St. Louis, and Memphis. From Dylan's childhood perspective, however, the road ran in a distinctly southward direction, down to the blues music that he so loved and that so heavily influenced him artistically.
The crossroads of Highway 61 and Highway 49 is where Blues legend Robert Johnson reportedly sold his soul to the devil to become a renown musician. Later Bob Dylan would "revisit" this highway which was the downfall of so many. You could call it Desolation Row because it would give you the Tombstone Blues singing the Ballad of a Thin Man whose destiny was to live Like a Rolling Stone. In his 2004 60 Minutes interview, when Dylan was asked by he still performs, he suggested that he made a similar deal with the devil. There are all kinds of miscreants on the album, but they all share one thing in common: having sold out to something. "I'm Going down to the Crossroads, just to beg a ride" sang Johnson and later Clapton. Dylan just happened to revisit the place.
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