I drove the first part of the famous Route 66 – with amazing pizza, alpine rollercoasters and NASCAR races
IN America, everything is bigger, including the roads – and I went to travel one of the country’s most iconic.
Following the lyrical advice to “get your kicks on Route 66”, I started out on the first stretch of the historic route through the state of Illinois.
Established in 1926, Route 66 was a pioneer among American highways. Though it was supplanted by a modern road network in the 1980s, the “Mother Road” still weaves through eight states, passing big cities and small-town America alike.
My journey started in Chicago, home of the skyscraper, where downtown is dominated by some of the best tall buildings in the world.
Having built the first skyscraper in 1885, the city still boasts 135 high rises. Shoreline Charters & Tours () offers architecture boat tours along the Chicago River, past the 1,451ft Willis Tower (formerly Sears Tower and the tallest on the planet for 24 years until 1998) and the 1,198ft St Regis Chicago, the tallest building designed by a woman.
The city is also famed for pizzas. Though traditionalists will like them flat, there is no getting away from the taste sensation that Chicago’s deep-dish creations deliver.
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For the city’s most famous pizza pie, try Lou Malnati’s Pizzeria in the upmarket Gold Coast neighbourhood. These thick chunks of gooey pizza take up to an hour to bake and taste incredible.
They also do hot dogs their own way, with the addition of ketchup being a culinary faux pas akin to wearing socks with sandals.
Instead, the standard-issue Chicago dog comes generously covered with mustard, bright green relish, freshly sliced tomatoes and, if you’re feeling adventurous, a pickled chilli. The result? A snack so refreshing, it’s like a summertime dip in Lake Michigan. To wash my hot dog down with a beer, I headed towards Wrigley Field, home of the Chicago Cubs baseball team, and a bar called Murphy’s Bleachers.
Inside is adorned with memorabilia that chronicles the team’s “cursed” history, which includes a 108-year wait for a World Series win.
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The rest of my trip was a dive into small-town America, where the food portions are big and warm, much like the local welcome.
First stop was Old Joliet Prison in the city of Joliet, 35 miles south west of Chicago.
Tough and down to earth
Built in 1858, the sprawling jailhouse, which was used in 1980 film The Blues Brothers and TV series Prison Break, has been turned into an Alcatraz-style tourist attraction since its closure in 2002.
Phones reportedly drain of battery in the execution chamber — presumably by ghosts sick and tired of social media-obsessed tourists snapping selfies.
From Joliet, it was a quick drive to Springfield, Illinois’ state capital, where President Abraham Lincoln practised law and where the Abraham Lincoln Presidential Library And Museum now stands.
The museum’s attractions were designed by the Walt Disney Company and help bring history to life, with talking mannequins and computer-generated imagery. To top it off, there was a 6ft 3in Lincoln impersonator talking to the patrons who was so convincing I thought, “This place must be haunted too”.
My biggest slice of Americana came at the town’s Route 66 Motorheads Bar & Grill, Museum & Entertainment Complex.
It feels like you’re walking through a biker gang hangout from a movie, but without the threat of a mass brawl.
It was lucky I was hungry when I tucked into the Horseshoe — an open sandwich with your choice of meat, covered in fries or tater tots (deep-fried clumps of potato) and a homemade cheese sauce.
But I still struggled to finish the beastly feast, which they say was inspired by Welsh rarebit.
The next day I travelled 60 miles south to the town of Livingston and the Pink Elephant Antiques Mall, which has a giant statue of Donald Trump out front.
Inside is a huge array of knick-knacks, including vintage homeware and pop culture memorabilia such as Blues Brothers and Lincoln merchandise.
I continued my journey south, hugging the Mississippi River and on my penultimate day settled in the sleepy town of Grafton, population just over 600. There you can ride a chair lift up to the stunning Aerie’s Resort, perched on a cliff with a panoramic view of the river and town below.
On the resort’s alpine rollercoaster, thrill-seekers can pilot their own cars along a 4,000-foot track that winds through a scenic forest.
I finished my trip in true American style with a day at a Nascar car race held at Madison Illinois’ World Wide Technology Raceway.
The 300-mile contest — that’s 240 laps of the oval track — featured around 40 powerful cars with crackling exhausts driving at speeds no amateur should ever attempt.
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Nascar is a uniquely American experience. While Europeans watch Formula 1 with drivers who live in tax havens in Monaco and Switzerland, American stock car racing has working-class roots in the south of the country. The drivers were tough and down to earth, just like the cars.
Whether navigating Chicago’s urban maze or soaking up small-town America, the Illinois Route 66 offers generous helpings that are sure to expand your horizons — as well as your waistline.
GO: ROUTE 66
GETTING/STAYING THERE: America As You Like It has a six-night Illinois Route 66 fly-drive from £1,170pp including flights from Heathrow to Chicago in March 2024, returning from St Louis on American Airlines. Includes five days’ car hire, two nights at the DoubleTree by Hilton Chicago Magnificent Mile, one night in Pontiac at the Hampton Inn, one night at the President Abraham Lincoln Springfield and two nights at the DoubleTree by Hilton Hotel Collinsville.
See or call 020 8742 8299.