A303

 Everyone has a favourite road (don't they?  just me then).
Motorways do a job, conveying the driver from point A to point B with relative ease (unless you're stuck in traffic jams, roadworks, or "Improvement Schemes" restricted the speed limit to 50mph for most of your journey.  Yes they do the job, but Motorways are quite dull.  The monotony may be broken every 30 miles or so by a Service Station but there ain't much to look at except the back of the car in front.
Before the motorways arrived - the first being the Preston by-pass in 1958, and then followed by a massive increase in miles of road over the next 15 years - the A Road (usually following established routes between major towns and cities, which in turn followed Stagecocah routes or Trade routes) was the road of choice.
And despite the appeal of the Motorway, the A Road offers a more relaxing and picturesque experience.  Service Stations may be further apart (or consist merely of a burger van in a layby), but the journey just feels more involved.

From where I live, there are 2 prime routes to travel west.

1. M4 & M5
2. A303

The M4 & M5 route may be quicker, but it's also 10 miles longer (and did I mention the dullness of motorway travel).  Also, you can never trust the traffic on the M5 south (even at the quietest times), and returning home going north is often as bad.
The choice is to take the hypotoneuse of the triangle and travel on the A303, and not purely for the Co-Op Distribution Centre south of Andover, Boscombe Down and Salisbury Plain, the sight of Stonehenge, and Mr Blobbys' former home at Cricket St Thomas.
It's a straight route with the momotony broken by regular roundabouts, and great lengths of dual carriageway which, despite the reputation of traffic jams, frees up traffic flow so it never truly reaches dashboard-banging proportions.
Another great attraction of the A303 was the regular appearances of Little Chef or Happy Eater - both long gone, and now replaced by Starbucks, Costa, or a scantly stocked BP Petrol Station.
The A303 also leads (with slight diversion) to Glastonbury - around June the stories of traffic congestion are no doubt true as (if all those that say they have gone are included) a quarter of the population of the UK decamps to the roadways.
It's possible that Glastonbury was the location in mind when Kula Shaker released "303" on their debut album
(then again, maybe like me they just like the road)

After backpacking around India for a year, Crispian Mills (son of actress Hayley Mills) returned to the UK and formed The Kays in 1993.  Their debut live performance was at that years Glastonbury Festival, but started to fall apart soon after.  Kula Shaker was the re-named, re-configured band formed after the fallout.  Fortuitously for the times, the mixture of psychadelia, Indian mysticism, themes, and instrumentation, bolted to a Britpo-esque attitude and sound proved a winner.  Kula Shaker benefited from rabid record companies signing up anytone who was British and played guitar.
Kula Shaker though stood out as there was a little more about them than some other fag-end of Britpop landfill.
Their debut album 'K' came off the back of 3 successful singles, and no little media exposure and critical plaudits.
The album became the fastest selling debut album in the UK since Elastica a couple of years before, and is actually a pretty good album ("Hey Dude" is one superb song that fitted the times just right).
And when the following year a cover version of "Hush" hit the Top 10 all looked good in the Kula Shaker garden, as success in the US appeared likely.
The second album though ' Peasants, Pigs & Astronauts' was not as well received, sold relatively poorly, and coupled with Crispian Mills comments about swastika imagery, saw Kula Shakers stock fall.  Although he qualified his statements, expressed his aplogies for his naivite, the damage was done and Kula Shaker ceased trading in 1999.

Kula Shaker - 303

Bob Dylan released 'Highway 61 Revisited' in 1965 - the name coming from the north-south highway that passes through his birthplace of Duluth, and winds along Mississippi River down to New Orleans. The route also passes near the the birthplaces and homes of  Muddy Waters, Son House, Elvis Presley and Charley Patton. There is also an intersection with Highway 49 - the crossroads where Robert Johnson (allegedly) sold his soul to the devil in return for increased playing ability (and no little future legend status).
Arguments rage as to which is the best Dylan album, but 'Highway 61 Revisited' contains "Like A Rolling Stone" so I think that should be enough to secure it's place.
In a roundabout homage to the album, John Otway recorded "A413 Revisited" documenting his return home to the Vale Of Aylesbury.

John Otway - A413 Revisited

Perhaps most famous road song is "Route 66" - Billy Bragg tended to agree so he took the tune and re-imagined the lyric travelling east from Docklands to Shoeburyness

Billy Bragg - A13 Trunk Road To The Sea