After an evening spent drinking and talking later than was sensible, the stranger's resolution to sort his life out struck a chord. Then it all came back to me. I'd failed to switch off the television before falling asleep and it had carried on all night without me. The old crooner in the box hastened my return to consciousness with a rendition of "Delta Blues" by the great Son House.
The winter sun had only just risen over the Mississippi Delta, and the thin curtains of my sharecropper's shack, one of half a dozen old dwellings on a former cotton plantation about four miles from the town of Clarksdale, Mississippi, were no match for the sharp light. The Shack Up Inn is the whim of Bill Talbot, a music-loving, pony-tailed entrepreneur who likes to collect things. Among the artefacts in my room were: a honky-tonk piano (minus two keys); an ancient gramophone with a supply of spare needles; some rusty crop-spraying equipment, and a giant brown fridge, circa 1950, still able to chill a Bud. The place is typical of the American South: quirky, spirited, rough around the edges, take it or leave it. I wouldn't have missed it for the world.
Clarksdale is the birthplace of Charlie Patton, the aforementioned Son House, Howlin' Wolf and John Lee Hooker. BB King worked in the fields nearby for a dollar a day. It also contains the famous crossroads where Highway 49 meets Highway 61. Famous, perhaps, but entirely bogus in its claim to be the place where the blues prodigy Robert Johnson made his legendary pact with the Devil, selling his soul for the gift of being the greatest guitarist of his generation. If that transaction ever did take place, it was surely not at one of the busiest junctions in the Mississippi Delta.
Tracking down the real crossroads is something I was forced to leave to lifelong blues scholars, just as I had to admit defeat in finding a connection between a single line of Bob Dylan's ground-breaking album and the highway after which he named it. Highway 61 Revisited was released 40 years ago this year. But the thoroughfare contains absolutely nothing at which the travelling fan can point and say, "This is what he was writing about". At least Lennon and McCartney left us Strawberry Fields and Penny Lane - places we can find on a map.
The real, asphalt Highway 61 is a rewarding road to travel on, providing you avoid it during the withering heat of summer. Technically it runs all the way from New Orleans in the Deep South to Chicago in the heartland, but the essence of 61 is the section that crosses the Mississippi Delta, starting at the languid, elegant ports of Natchez and Vicksburg and finishing up in throbbing, edgy Memphis, just over the border in Tennessee.
The towns along the way reflect both the wealth and the poverty of the South. Natchez capitulated so quickly in the Civil War that many imposing antebellum houses remain. Port Gibson was left untouched by the advancing Union army because General Grant declared it "too beautiful to burn". Vicksburg is another attractive riverside spot, with numerous big houses converted to B&Bs. At this point, heading south to north, the Highway branches off, leaving the river a few miles to the west, and gets to the heart of the matter.
The Delta has one of the most unremittingly monotonous landscapes on Earth. The Highway runs dead straight for mile after mile, with nothing to see but telegraph poles and lonely intersections. Life here, for the early 20th-century sharecroppers, was desperately hard; as you drive through this brooding, primordial place, you can sense the hopelessness they must have felt, digging, planting and lifting their infinite rows of cotton. Music was their consolation and, for a few, their means of escape.
At Greenwood, I was invited to join some well-to-do locals at the Cotton Row Club, where liquor can be consumed as long as the bottles are disguised in brown paper bags. Lawyers played cards with labourers, but the only black man was washing someone's boots. Across town, I found a live performance by two bluesmen - father and son - but throughout the Delta I was told the traditional juke joints are closing down by the dozen.
"The kids today, they just want their rap," said a white-haired onlooker. "If this generation stops playing, this music of ours will soon be dead." I heard that lament more than once, but there are some encouraging signs. A few miles further on, the town of Leland has opened a Highway 61 Blues Museum, and has been staging an annual music festival for the last five years.
Clarksdale, poorer and scruffier than its southern neighbours, is the undisputed blues HQ, with a highly regarded museum of its own, and the Ground Zero Blues Club on Delta Avenue, part-owned by the actor Morgan Freeman, stages live music two or three times a week. A few miles north of Clarksdale, the Blues Highway crosses the state line into Tennessee and enters the outskirts of Memphis, where American civil rights took wing. For Bob Dylan in 1965, a backwoods boy from Minnesota still discovering the world, that was something for the future.
Shack Up Inn (001 662 624 8329; www.shackupinn.com), double shacks from $50 (pounds 28) per night. Highway 61 Blues Museum, Leland, open Tues-Sat 10am- 5pm (001 662 686 7646; www.highway61blues.com); entry free. Delta Blues Museum, Clarksdale (001 662 627 6820; www.deltabluesmuseum.org); open Mon-Sat 10am-5pm; $6 (pounds 3.30). Ground Zero Blues Club, Clarksdale (001 662 621 9009; www.groundzerobluesclub.com).
More information from Mississippi Tourism: 01462 440 787; www.visitmississippi.org