From Chicago to Springfield - America's everytown

And so the journey begins. Almost two-and-a-half thousand miles (or 40000km) of the American heartland, from the south-western shore of Lake Michigan to the Pacific Ocean as it laps beneath the uprights of Santa Monica Pier.

Along the way I will pass through eight states and three timezones, driving along a road that, though decommissioned in 1985, remains intact for 85% of its original route.

Today, despite being signposted, Route 66 is more of an ideal than a practical means of getting from one place to another.

After all, if you wanted to drive from Chicago to LA in a mindless dash along the I-55, 44, 40, 15 and 10 interstates, you could do it, without stopping, in 31 hours.

This, on the other hand, provides a totally different experience. Driving Route 66 might sound like a cliché of bandana-wearing fiftysomethings on newly-bought Harley-Davidsons - and that's OK if that's you - but to this traveller, it's about seeing a bygone America still embodied by milkshake drive-ins, wholesome, home-grown fare-serving restaurants, churches and schoolhouses that still line the road.

© Simon Poulter 2013

The first leg has been a gentle, 200-mile stroll out of the Windy City and onto Main Street USA where it separates away from I-55 and starts snaking through rural Illinois. Like a mother not wishing to stray too far from a child on its first day at school, 66 checks in with 55 at various points.

The flat, sprawling hinterlands below Chicago are largely unspectacular. They're not meant to be anything else. But, as you trundle alongside the freeway at a modest 45 miles an hour, the clapboard houses, lawned frontages and cute little communities remind you that there's a reason you've chosen old over new.

It does, however, feel a little like walking through Business Class to take your seat in Economy. That was, of course, the main intention of President Eisenhower's interstate highway system, an upgrade to America's motoring arteries, but as with most modernities, there's always a tradeoff.

© Simon Poulter 2013

As you head south, farming and various forms of light industry dominate the land, further reminders that Route 66 isn't a theme park. Soon you find yourself in Joliet. I mention this only because, having watched The Blues Brothers a zillion times over the last 30 years, I am familiar with the fact that, until recently, here functioned the Illinois State Correctional Center where John Belushi's 'Joliet' Jake Blues was picked up in an old Mount Prospect city police car by his brother Elwood (named after the nearby town thereof).

Before you know it, you're out the other side, cruising through cute, lawned communities where ordinary life goes on within -"moms" ferrying children to "soccer" practice, workmen nailing stuff, mechanics fixing cars. Normality breeds further normality.

Which makes it entirely appropriate that the first leg of my drive on Route 66 should end in Springfield, the Illinois state capitol. It is as American heartland as it is possible to be. Indeed, it is one of 29 Springfields across the United States. 30, if you include the fictional setting of The Simpsons.

Creator Matt Groening grew up in Portland, 100 miles north of Oregon's own Springfield. But, he told Smithsonian magazine last year, after 25 years of speculation, the real inspiration was the sitcom Father Knows Best, which took place in a place called Springfield. "When I grew up, I realised it was just a fictitious name," Groening said. "I also figured out that Springfield was one of the most common names for a city in the U.S. "In anticipation of [The Simpsons'] success, I thought, 'This will be cool: everyone will think it's their Springfield.' And they do.

Actually, if I were to be very picky, America's founding fathers didn't exactly stretch the grey matter when it comes to naming places. You have, for example New Amsterdam, which became New York, and most of the north-eastern seaboard is named after Old England. Furthermore, I began the Route 66 journey on East Adams Street in Chicago and have ended up at a hotel in Springfield located at 700 East Adams Street.

You can't, by the way, miss this particular hotel. At 30 inexplicable stories high, the Hilton Springfied is the tallest skyscraper in Illinois outside of Chicago and the tallest in Springfield itself. Which is not a difficult achievement as it is the only skyscraper in Springfield. You can trust me on this one, you won't need sat-nav to find it.

To say this is an incongruous feature of Springfield is an understatement. It actually looks like something dark and evil erected by Monty Burns in the fictional, cartoon Springfield. To add to the menace, on arrival, the hotel is crawling with cops. Literally.

I am later relieved to learn that they're not actual police officers, but members of the Illinois Law Enforcement Explorer program, a kind of cop cadet force of teenagers who may, when they turn 21, apply for jobs with the local police departments they represent. They're in Springfield for their bi-annual conference, learning about how to deal with traffic stops, bomb threats and hostage negotiations, the sort of typical day, really, in the life of the American cop.

But I digress. My visit to Springfield isn't to feel uncomfortable under the collar by having soon-to-be gun-toting teenagers swarming about the place, but to visit this particular Springfield's place in American history. And in that respect, the Hilton - despite its disfiguring presence on the city's skyline (in fact, it is the city's skyline) - is ideally located to visit all of the main landmarks in one go.

© Simon Poulter 2013

Springfield, IL, trades quite openly off both its location on Route 66 and its association with "America's favourite president" (sorry Bill), Abraham Lincoln. Abe lived here from 1837 until 1861, when he became the country's 16th president and, as Steven Spielberg's Oscar-winning, but buttock-challenging film retells, leading the US through the Civil War, maintaining the Union, abolishing slavery and transforming the national economy. All before he was shot at the theatre four years later.

Lincoln is everywhere. You can't walk past a storefront without seeing that jutting, bearded jawline and famous top hat. Springfield's official tourist blah promises that "...you’ll feel as though you’ve stepped back in time…experiencing Springfield as Lincoln knew it.", which is not really that accurate: I'm fairly sure that in Lincoln's day there were considerably fewer hotels, especially those cluttering up the view, not as many branches of Starbucks, and considerably more horse manure and other unpleasantries clogging up the streets.

There is, though, plenty to indulge the historian, from Lincoln's family home to his tomb at Oak Ridge Cemetery, along with the Old Illinois State Capitol building and the Abraham Lincoln Presidential Library and Museum, containing the world’s largest collection of documentary material related to the life of Abraham Lincoln, including an original hand-written copy of the Gettysburg Address and the pen he used to sign the Emancipation Proclamation.

Just 60 years after Lincoln became president, another American milestone took place: the first drive-through burger bar, the Maid Rite Sandwich Shop, opened in Springfield, launching an ever-lasting national obsession with motor-borne convenience, from drive-through coffee shops and pharmacies, to drive-through ATMs which include instructions in Braille. Think about that for a second.

And while you're indulging in nostalgia, another must is Shea's gas station, Bill Shea's museum of life alongside Route 66 featuring more than 50 years of, well, gas station memorabilia. Even if a little hokey, it's another reminder of what Route 66 represents. A more innocent time, before the world was swallowed up by omnipresent corporations and brands, the time that this journey is already doing a great job in connecting me with. On to "Saint Looey".

Tomorrow: WWDBD? is only 24 hours from Tulsa