Travel: Route 66

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 on America’s Mother Road, cutting a path from Chicago to St. Louis, studded 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 suburbs 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.  

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. 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. I managed to park myself in one of them. 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. 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 holds huge 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. 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.”  

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. 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. 

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.