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Route 66 in 66 hours: How to conquer America's iconic highway in a long weekend

This 600-mile loop is a thrilling microcosm of the Mother Road
This 600-mile loop is a thrilling microcosm of the Mother Road Credit: ADAM ALEXANDER PHOTOGRAPHY
Is it possible to capture the essence of America’s most iconic highway in, say, 66 hours? It is if you have the inside track 

The automobile is so much more than a means of getting from A to B in America – it’s the freedom to roam a sprawling, intrepid, confused, disparate union. This vast country has been traversed by the settlers who arrived on the East Coast and pioneered into the prairielands of the Midwest; by the Gold Rush crowd clamouring their way to California to find their fortune; and by Prohibition convoys seeking new thoroughfares to negotiate by night.

Route 66 encapsulates these ways of life like no other. Built in 1926, it was the main artery between Illinois and the West Coast, bringing Dust Bowl and Great Depression migrants from the Midwest to the sunlit uplands of California. Popularised by John Steinbeck, among others, it now has a historical designation – no longer an official thoroughfare – preserved and protected by its iconic status.

What better way, then, to see if the true America still exists, than driving Route 66? It’s a bucket-list trip – but a very long one. Could there be a way of getting the feel of the road, a sense of place, within the sort of timespan and budget that doesn’t eat too much into your annual leave and your bank balance? Perhaps, just because it sounds appropriate, you could get a feel for it in 66 hours?

Attempting to drive the 2,448-mile (3,940km) strip – from Chicago to Santa Monica – in under three days would be pretty much impossible, definitely stupid, and possibly fatal. So, what I planned to do was take on the sweeping plains and prairies of Illinois, looping back to Chicago on reaching the southernmost tip of the state. This would be a microcosm of the Mother Road – a 600-mile round trip that would take in prison visits, electric storms and a 30ft spaceman… and that was just on day one.

First, I spent a night in the Windy City. I checked into my hotel, just off the tulip-lined shopping hub of the Magnificent Mile – all wide sidewalks, soaring edifices and flagship stores. Dazed and discombobulated through a combination of skyscraper-induced vertigo and creeping jet lag, I found myself, two hours after arrival, at the other end of the Mile, descending the ornate stone steps of the Riverwalk to the Shoreline Architecture River Cruise. It turned out to be the ideal way to cleanse the mind of an eight-hour flight. I got to know the city almost brick by brick, while bobbing along and relaxing with a cold drink.

Chicago by riverboat, the ideal way to recover from a long flight Credit: istock

Disembarking through a cascade of bubbles blown by a busker, I moseyed (one moseys in the Midwest) back to the hotel. Dining lakeside later that evening – with the Navy Pier Ferris wheel and the blinking lights of the cityscape reflecting on the surface of Lake Michigan – I felt ready for the Mother Road.

Early next morning, I started where Route 66 begins. Lou Mitchell’s diner – festooned with motoring paraphernalia – bustled with morning meetings, road trippers, and waitresses with name badges brandishing coffee pots as if they were an extension of their own arms. Opting for the French toast and bacon, I took full advantage of the coffee refills.

It goes without saying – well, almost – that if you plan to drive Route 66, you should be picturing a Mustang, a Dodge, a Cadillac and, my choice, a Chevy. The one I decided to rent was a new Camaro. In truth, this was a compromise – tempting as it was to scout a Fifties muscle car, the lack of satnav, air-con or any practical knowledge of how to fix a broken-down classic car on the side of a freeway swayed me towards the more modern iteration.

So, off I went… under sunny skies, negotiating Chicago’s morning crush. The traffic melted away as I headed out of town along the old road – as open as Hollywood had promised.

Then the clouds gathered, swiftly turning a shade of apocalypse yellow-grey. You can see weather coming a long way off on the plains of the Midwest, and as I pulled up to Old Joliet Prison, it came to join us.

The prison (picture Downton Abbey with barbed wire), which has provided accommodation for some deplorable characters, and also served as a backdrop for The Blues Brothers and Prison Break, is now undergoing refurbishment to turn it into a fully fledged tourist attraction. I received the quick “it’s about to chuck it down” tour, taking in, most chillingly of all, the pitch-black operating theatre. I was fittingly unnerved… especially when, right on cue, the thunder started. And then prolific rain; lightning forks dancing on the horizon – a Midwestern spectacle. 

Three minutes after turning out of the car park, I pulled into a lay-by. There was no chance of any progress until I could at least see where the stop signs were through the sheeting rain. So, relishing what the Illinois climate was going to throw at me next, I refuelled at the Launching Pad Drive-In, under the 30ft Gemini Giant and pushed through, in pioneer style, to my final destination of the day.

Old Joliet Prison has provided accommodation for some deplorable characters Credit: getty

Not before a stop in Pontiac, however. It’s what you might call a “one-horse town” (albeit one named after an assassinated Native-American chief). Stars and Stripes hang proudly over a sleepy Main Street, pickup trucks wait at the stop signs, windows down, country and western music blaring out of the car speakers, while God-botherers cross the road, eager to recruit you… this is an America you won’t see in the city. Pontiac has the largest Route 66 mural on the road, offering the ideal backdrop to show off the Chevy at its shiny best, especially now the clouds had been chased away by intense Illinois sunshine.

After seven hours of driving that day, I arrived in Springfield and the Abraham Lincoln Hilton DoubleTree. That day had been my first time driving on the right-hand side of the road; my first negotiating an electric storm; and my first eating a tuna sandwich under a giant fibreglass statue. What I needed was a walk.

Springfield (there are many, many Springfields in America) is a gentle town, reminiscent of its namesake in The Simpsons. After consuming a “horseshoe” (a patty on sliced bread, both of which are then obscured by fries and a “cheese” sauce), I did some more moseying – to Abraham Lincoln’s house, a weatherboarded family home where he lived as a practising lawyer, the only home he ever owned.

Springfield, a gentle town, reminiscent of its namesake in The Simpsons Credit: getty

Thirty hours into my trip, and following a blackout sleep and a whistle-stop visit to the Abraham Lincoln Museum, I was on the road once again, driving along one of the few stretches of the Route still constructed from the original Twenties red bricks. I dashed to Alton (at the legal limit, of course), kicking up dust, passing “Guns Save Lives” roadside signs, with bright sunlight bouncing off the gleaming hood.

Those I spoke to in Springfield took quiet satisfaction in telling me that Alton had been flooded recently, standing as it does on the banks of the Mississippi. Small-town rivalry looms large, and there is a strong sense of identity and civic pride tied to every place – tribal, protective, American.

The floods had subsided, leaving Alton (birthplace of Miles Davis) mellow, green and lush, with a sense of the Deep South slowly emerging. This is a place of lazy sun; wooden-clad houses fronted by stoops with rocking chairs; Stars and Stripes fluttering in front yards. Tucked away was Beall Mansion, where Sandy and Jim welcomed me into Edwardian splendour, including a chocolate buffet, brandy in crystal decanters, and a Steinway piano. There were very few surfaces untouched by lace. 

Next morning, there was time to take in the Mississippi. On the other side was Missouri – Illinois was done. There’s something very spiritual about standing on the edge of this legendary waterway – a sense of music, history, endings, beginnings, destinations reached, the road still to come.

Chicago was my finishing line now. A storm came again, the “open” road now nothing but a vague silver track in an impressionist painting. I pressed on – eyes squinting, hands gripping the wheel, shoulders tense, music turned down – finally arriving three hours late to hand over the Chevy, wishing it a fond farewell and thanking it for leaving me a little more James Dean than it found me.

Back in the familiar embrace of the city, a night at the excellent Hoxton – newly opened in the fashionable Fulton Market District of Chicago – helped to blur the lines between Americana and English sensibility, as my flight home loomed.

Full circle Credit: getty

There was a sense of achievement, of fulfilment – of seeing an America thought almost lost, an America you wouldn’t see or feel in a city or at a resort. It’s a country founded on wandering, wondering, persisting and pushing, and you could feel this with every mile driven, every stop visited. I’ll give myself a bit longer next time, though. 

The essentials

Getting there

British Airways (0344 493 0122; ) flies up to six times daily from London to Chicago via its transatlantic joint business partnership with American Airlines, from £297 return. 

America As You Like It () has Route 66 packages from £605pp.

Driving the Route

Premium car hire is available from Hertz Gold at .

Pit stops

Lakefront Restaurant boasts “casual elegance” (meaning multi-screen sports shown), and introduces you to Midwest portion sizes ().

Obed & Isaac’s, said to be the best “horseshoe” in Springfield, this welcoming microbrewery does a good line in flatbread pizzas too ().

Motorheads Bar and Grill. Owned, built and curated by Ron, this labour of love offers good eats in a motor-themed bar. Nip out back to see the Americana he has acquired over the years ().

Old Bakery Beer A microbrewery serving hearty modern food, owned and run by Lauren and James, who must be the only vegans in Illinois ().

Dell Rhea’s Chicken Basket. The oldest fried chicken joint on Route 66, this place is part of the Route 66 Hall of Fame. Ask for warm biscuits – scones ().

Tortoise Supper Club. Finish your time in Chicago with the sound of jazz in this stylish establishment ().

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