Monday 29 October 2018 2:27 pm

How much of Route 66 can you see in one weekend? We head to Chicago to find out…


Route 66, America’s most legendary highway, is a month-long mission for many who attempt to drive the whole thing. It starts in downtown Chicago and ends 2,448 miles later in front of the Santa Monica Pier in Los Angeles.

But what if you only have a weekend to Get Your Kicks on Route 66? With cheap flights to the Windy City every day from Gatwick with Norwegian and a fleet of muscle cars waiting in the rental section at O’Hare, I set myself a mission: To experience as much freedom, blues and apple pie as possible just on the Illinois leg of the Mother Road.

The car, chosen from Hertz’ Adrenaline Collection, is inspired by my favourite cult road trip movie, Vanishing Point; a white Dodge Challenger R/T. My reading material for the truck stops; Jack Kerouac’s On The Road. A road trip in USA should go beyond sightseeing – it’s about living pop culture.

The route takes me from Chi-town to St Louis, 300 miles away, stopping overnight in Pontiac and Springfield. The road starts directly in front of the Chicago Institute of Art and, conveniently, within two blocks passes the first of several legendary diners. Lou Mitchell’s is the first fuelling stop for almost every traveller on ’66, thus finding itself on the National Register of Historic Places. Founded in 1923, they hand out fresh donut holes to people waiting in line. I order the Denver omelette and unfurl my map, plotting the day’s stops.

The first is the very opposite of freedom. Joliet Prison, just beyond Chicago’s city limits, has a fascinating and scary history. Closed since 2002 it’s largely been used for smoking crack since, but it’s also been a major filming destination. Prison Break was shot here, and you can arrange a private tour. Most of my questions are centred on murders (many), ghosts (reputedly), and what happened when John Belushi and Dan Aykroyd came here to film the opening scene of The Blues Brothers. In honour, there’s a mural of the pair on the street outside.

Parts of Route 66 no longer exist. There are a couple of sections where one’s forced to take Interstate 55, but the highway is almost uninterrupted from Joliet down to the Mississippi River. It is lined with antique gas stations, retro burger joints and famous ‘Muffler Men’. These roadside attractions, fashioned in the 1960s, are enormous fibreglass sculptures of fictional heroes such as Paul Bunyan, and are placed outside restaurants in the hope of luring people in. Three appear along Illinois Route 66, the first being the Gemini Giant in Wilmington. The 30ft high spaceman holds a silver rocket ship in his hands, advertising the Launching Pad drive-in.

I stop for a cheeseburger at the Polk-A-Dot diner, a ‘50s time machine with its Elvis and Marilyn manikins and memorabilia. The jukebox is well-stocked, like the soundtrack from Back to the Future.

Route 66 is lined with museums, most of which are to itself, and the best in this state is found in Pontiac. Here they have a camper truck, converted from a school bus, that was owned by artist and cartographer Bob Waldmire and drove the full length of Route 66 hundreds of times, from which Bob painted scenes from the road. Waldmire, who died in 2009, is something of an icon in these parts. A true eccentric, he inspired the hippie character ‘Fillmore’ in the Pixar movie Cars. Eccentrics abound along this stretch of blacktop. Henry’s Rabbit Ranch, for instance, invites you to inspect one man’s furry friends, along with his unrivalled collection of rusting Volkswagens. Pontiac also has a museum dedicated to the car brand that takes its name. Comparing the 1990s models here to those on display from the 1950s, 60s and 70s proves that progress doesn’t always go in the right direction.

My Dodge Challenger, on the other hand, is a rather brilliant re-interpretation of the 1970 pony car that inspired it. Its 5.7 litre V8 sounds like thunder and produces 375bhp, leaving thick ribbons of black rubber in its wake. It does have its foibles, though; you could lose a juggernaut in its blind spots.

Illinois’ state capital is Springfield, where Abraham Lincoln lived, practised law, and is entombed. The blocks surrounding his clapboard home are preserved just as they had been when the 16th President left for Washington in 1861. Springfield is a handsome, buzzy town filled with craft microbreweries and bars. The Buzz Bomb Brewing Co serves an American Pale Ale called Mother Road, inspired by Route 66. Nutrition comes in the form of a deep-fried corn dog at the Cozy Dog drive-in, founded and still run by the family of artist Bob Waldmire.

Surely the finest culinary contribution this town has made to the world is the Horseshoe: thick-cut toasted bread, two hamburger patties, French fries, and a tonne of American cheese. A bit like a croque monsieur mated with a McDonalds. They do a particularly heart attack-inducing one at the Ariston Café in Litchfield, which has been keeping Route 66ers stuffed since 1935.

I meet up with some enthusiasts from the Cool Cruiser Car Club. JC Hardy and his girlfriend Marcia own the Dr Pepper-coloured ’63 Chevy Impala and give me a ride to experience one of the most atmospheric parts of the Route. Between Springfield and Litchfield is one of the only remaining stretches of original brick road, completed in 1931 in Auburn. There’s very little infrastructure around here – no strip malls, no gas stations, no Hampton Inns – just cornfields, so it really does feel like John Steinbeck’s The Grapes of Wrath.

Back in the Challenger, I’m into the final furlong. The arch of St Louis hones into view. Here, Route 66 splits into divisions. I park up and walk the original Chain of Rocks bridge which crosses the epic Mississippi. Taking the river route affords some of the best views in the Midwest. Harley-Davidson riders cruise along the waterside, and I follow them past the giant mills that rise above Miles Davis’ birthplace, Alton.

In 300 miles I’ve seen the sights and sounds that inspired a lifetime’s literature and road movies. I yearn to do the whole thing, from Lake Michigan to L.A. But doing it one stretch at a time gives one a chance to savour it, and digest all those Horseshoes.


This Saturday, the Regent Street Motor Show is showcasing Route 66 and the cars that have made it famous. Visit

For more information on Illinois and Route 66, visit

Norwegian flies to Chicago from Gatwick from £150 one way in economy. Visit

Car hire from Chicago O’Hare Airport costs from £27 per day. Challengers, Corvettes, Cameros and Mustangs are available in the Hertz Adrenaline Collection at For further USA road trip inspiration head to the Hertz American Road Trip Planner.

Tour packages are available at