For the Love of Travel
For the Love of Travel

Illinois Route 66

Do you fancy sampling a taster of America’s Mother Road, Route 66? Illinois ticks all the boxes, capturing the essence, the kitsch and evocative spirit of America’s greatest byway. A rendezvous with Route 66 is as classic as it gets.

Far from the madding crowd and those soulless six-lane interstate highways, it’s all about small-town main streets and quiet country byways on Route 66. Bookended by Chicago’s big shoulders and the sun-kissed palm trees of Santa Monica, you’ll need weeks to traverse the full-length of this 92-year-old, 3800km cross-country route.

But I got my proverbial kicks on the first 500kms of the route, cutting a path from Chicago to St. Louis, which is loaded with retro American delights aplenty. True to the spirit of the full Route 66 experience, the diagonal course of the highway was purposefully designed to stitch together rural towns, uniting them with a shared national highway system.

In 1926, the Illinois stretch of US 66 was already paved in concrete and the first state to claim it was “slab all the way.” A plethora of roadside services soon sprouted up. Food, lodging, auto services, souvenir shops, roadside attractions….the travel industry was born.

After making our way out of the suburban of Chicago’s southern flank, we followed the old route southwest from Joliet through a series of sweet little towns, popping up between the infinity sprawl of cornfields, stretching as far as the eye could see across the pancake flat expanse of the Mid-West.

It’s now officially designated as Highway 53, but the Historic Route 66 signs are ever-present. Our first stop was Wilmington where a 30-foot tall, bright green roadside statue soon captivated proceedings. Towering above the old Launching Pad Drive-in Restaurant, Gemini Giant is a lofty fibreglass spaceman, erected during the giddy heights of the space age.

He still commands court as a wildly popular selfie stop. As we prepared to pose in front of Gemini, the restaurant owner breezed outside to greet us and offered to our group photo. Such outgoing friendliness and hospitality, we soon discovered, was ever-present all along Route 66. Further up the road, we popped into Nelly’s Café, ablaze in retro memorabilia and buzzing with happy diners.

Their angus beef burgers are irresistible. Once again, we were urged to sign their guest book, as we did in every Route 66 attraction – and a quick flick through the pages revealed a regular supply of passing Kiwis. The guest books are like a thumbs-up throwback to the pre-Facebook and Trip Advisor era. If you’re partial to retro-themed cafes, the neighbouring town of Braidwood is home to the fiendishly popular 1950s-styled Polk-A-Dot Drive-In, with a giant of their own: a 9-foot-tall guitar-wielding Elvis Presley.

Few sights encapsulate the romance of the historic highway in more stirring fashion than the pint-sized roadside service stations. Two great specimens, that have been lovingly preserved and restored can be found in the neighbouring towns of quaint and leafy Dwight and Odell.

The Dwight Texaco station first opened during the Great Depression, managing to stay in business until 1999 – earning it the reputation as the oldest continually operating gas station on the Mother Road. It’s now been restored to its 1940s appearance, with vintage bowsers, and doubles as a visitor centre. In Odell, the Standard Oil gas station is even more picturesque, a classic 1930s station with an architectural style known as a “house with canopy.”

Another essential photo-stop and visitor’s book to sign. A short hop led us to Pontiac, which instantly seduced me as a heart-stealing Route 66 town. Bright, colourful and charismatic, Pontiac plays up its Mother Road credentials with irresistible panache.

19 giant wall murals evoking the glory days driving on Route 66 carpet the streetscape in the historic district. Miniature classic cars have been installed on the sidewalks, paying tribute to the American automobile industry and the glorious vehicle models that once purred through these streets. Parked up outside the Route 66 Hall of Fame and Museum, is Bob Waldmire’s 1966 Chevrolet school bus.

Bob was one of the leading preservationists of the historic highway, celebrating the history and richness of Route 66 through art. Another of his road-touring vehicles, a 1972 VW Microbus was immortalised in Pixar’s Cars movie, serving as the inspiration for the character, “Fillmore.”

Bob’s last commissioned artwork is the 66-foot long map of the highway adorning the side of the museum on Main Street. Too sick to paint the mural himself, his family and 500 friends from all along Route 66 gathered in Pontiac in 2011, to paint it in his memory. Another must-see is the Pontiac-Oakland Automobile Museum which boasts one of the world’s greatest collections of antique and classic Pontiac and Oakland vehicles, from General Motors, beautifully showcased in themed settings from across the decades.

Heading south, we called into Atlanta to size up Tall Paul, the former Bunyan’s Giant brandishing a hot dog. Main Street is bedecked with more evocative murals and it’s also home to one of the best Route 66 eateries. Palms Grill Café has been restored to its circa 1934 appearance where you’ll be served by wait staff in period uniform, while 1940s tunes sing out.

After refuelling on a thick slab of gooseberry pie, we then ventured to the only town named for Honest Abe during his lifetime – Lincoln. He supposedly baptised the place by spitting out a mouthful of watermelon seeds, hence the plaster watermelon and historical plaque, honouring the event. Lincoln also proudly boasts the world’s largest covered wagon, as certified by Guinness, suitably being driven by Honest Abe.

Add that one to your selfie stops. Further down the road, the state capital of Springfield is holds major pull among Abraham Lincoln aficionados. He lived and worked here from 1837 to 1861, leaving Springfield upon his election to the presidency. The holy trinity sights comprise his presidential library, his home and Lincoln’s Tomb. He was buried here after his assassination at the end of the Civil War.

Touch the nose on the bronze bust of Lincoln and good luck will follow. Well, so the legend goes. Before departing town, make tracks to a celebrated Route 66 Diner, the Cozy Dog Drive-In. Founded in 1949 by the father of Bob Waldmire, Ed is lauded as giving birth to that cherished Mid-West staple, the corn dog.

In these parts, the snack is simply called a “Cozy.” In addition to chomping down on a corn dog or two, the restaurant is chock-full of Route 66 mementos, signage and retro artefacts. Leave room in the tummy for one more roadside stop, if you’re day-tripping to St. Louis, because another superlative Route 66 dining experience beckons in Lichfield.

The Ariston Café is reputedly the oldest operating café on Route 66, as old as the Mother Road and still run by the family descendants of Peter Adam who first opened it. The menu is a step-up from the usual roadside fare, with white linens, refined décor and hearty hospitality completing the picture.

Our effervescent waiter, Logan, enthralled us with his humour, grace and sparkle. He was straight out of Disney central casting. The last gasp of Illinois’ Route 66 encounter climaxes on the banks the Mississippi River, where the state line rubs shoulders with Missouri.

Spanning the river is the historic Old Chain of Rocks Bridge, built in 1929 to spirit Route 66ers across the might Miss. This marvellous mile-long bridge has a 30-degree angled bend mid-way – the cause of many a crash.

Today, it’s off-limits to motorised traffic, but swooned over by recreationalists as one of the world’s longest cycling and pedestrian bridges. If you’re feeling particularly virtuous, you can actually follow the river cycle trail all the way to the Gateway Arch in St. Louis, on the 11-mile long track. As the lights of St. Louis flickered on the horizon, our riveting rendezvous with Route 66 from Chicago left us with a warm, satisfying and lingering glow.

Air New Zealand will start operating non-stop services between from Auckland and Chicago flying up to three times a week from 30 November 2018. One way Economy fares start from $1,019 (including taxes). Fares are also available via Los Angeles, San Francisco and Houston with onward connections to Chicago on partner airlines. Visit to book or for more details.

I organised my American rental car through Expedia, who offer a great range of sharply-priced car hire rates, no matter where you are travelling to. Did you know on Expedia you can get discounted rates on a great range of hotels when you add on to your existing trip? It’s called the Expedia Add-On Advantage. Book your flight, car or package on Expedia and you’ll instantly unlock up to 49% off select hotels until the day of your trip. Fill full details jump to

By Mike Yardley.