Laura Millar gets her motor running on a quirky, nostalgic journey from Route 66's origin in Chicago, across the state of Illinois - all over a long weekend.

For a sign with so much significance, it's not very impressive; small, brown and white, it's stuck way up on a pole on the corner of a busy Chicago intersection, between Adams St and Michigan Ave. But this sign commemorates the starting-point of one of the world's best-known roads: Route 66.

This 3900km route, which connected America's gritty east coast to its sunny west, officially came into being in April, 1926. And, practically since its inception, it's inspired - or been featured in - movies, songs, TV shows, and become the shorthand for a certain type of nostalgic, kitsch Americana, instantly recognised all over the world.

Historic Route 66 begins in Chicago, Illinois, and travels through to Santa Monica, California. Photo / 123RF
Historic Route 66 begins in Chicago, Illinois, and travels through to Santa Monica, California. Photo / 123RF

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I'm not immune; even though I'm not from the US, I've grown up with images of diners, neon signs, vintage cars and endless tarmac stretching into the horizon - symbols of freedom and adventure.

Oddly, Route 66 is not one, continuous road; its creation was, essentially, the linking together of smaller, existing ones. It was technically decommissioned in 1986, and is no longer maintained by the US Highway System. As a result, parts of it aren't driveable, but Illinois has 480 good kilometres, so my partner and I are starting at its east coast origin, and plan to cover it over three days.

We kick off the way most people used to fuel up before they hit the road - with a hearty breakfast at Lou Mitchell's, on W Jackson Blvd. Open since 1923, it's famous for its freshly-baked doughnut holes and jumbo omelettes, while its sassy, gum-chewing waitresses and chrome fixtures get my retro diner fixation off to a good start.

Driving out of Chicago - unfortunately not in a vintage Mustang, but a more prosaic Chevy Cruze - the skyscrapers fall away, replaced by a succession of small towns, which we soundtrack with fitting local radio stations, such as "50s on 5" and "60s on 6".

The occasional brown and white sign flashes past, reassuring us we're going the right way, and before too long we pull up at the Old Joliet Prison, a hulking, Gothic building whose claim to fame – apart from being one of the first prisons in Illinois, built in 1858 - is being used as a location in cult movie The Blues Brothers. Still in use until 2002, it was abandoned, occasionally invaded by squatters and illegal ravers; today there's a lot of Instagrammable graffiti and crumbling, peeling walls.

You can take a tour (jolietprison.org, tickets from $20pp), which reveals not only some surprisingly elegant architecture – the prison chapel is designed in mid-century modern style - but also some of the eeriest spaces I've ever seen, from the abandoned hospital block featuring one room with restraints on the walls, to the downright sinister solitary block.

Back in daylight, and 30km on, rounding a bend in the road by the tiny town of Wilmington, a strange sight looms before us. It's green, humanoid, and 9m tall. This is the Gemini Giant (named after the 1961 Gemini space programme), one of the original fibreglass "Muffler Men" that used to line the route to attract motorists' attention to a small town's local business. This one's next to the Launching Pad, a diner that originally opened in 1956, but eventually closed down in 2007.

Laura Millar in the tiny town of Wilmington, Illinois. The Gemini Giant is just one of the strange sites you'll see on a drive on Route 66. Photo / Supplied
Laura Millar in the tiny town of Wilmington, Illinois. The Gemini Giant is just one of the strange sites you'll see on a drive on Route 66. Photo / Supplied

In 2017, the abandoned building was stumbled upon by couple Holly Barker and Tully Garrett, who bought it – and the Giant - and set about restoring it to its glory days, with some of the original 50s decor. They're the first of several people we meet along the way who're investing in the Mother Road's future.

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"We get a lot of local customers, as well as people from the wider state who are only just realising that Route 66 is in their backyard," says Tully. I can vouch for their insanely-good pot roast sandwich ($8.66 – adorably, all their prices end in 66).

An hour away is Pontiac, home to 27 large murals commemorating the route, and the Route 66 Museum, stuffed full of memorabilia - from menus from long-ago-closed restaurants to photographs, maps and more. Volunteer Ellie explains, "the route really became popular in the dustbowl era, when people from the depressed Midwest used it to get to California to find work. In the 40s it was used to move troops around. And after the war, baby boomers used it for leisure travel." Today, they still do.

Route 66 mural, one of 27, in Pontiac, Illinois. Photo / Getty Images
Route 66 mural, one of 27, in Pontiac, Illinois. Photo / Getty Images

Later that afternoon, we reach Springfield, the Illinois state capital – where Abraham Lincoln lived for 24 years - and check in to the Inn at 835 (connshg.com/inn-at-835/, rooms around $104pn), before making our way to Motorheads Bar and Grill (66motorheads.com) just off the route, for dinner. It has a classic roadhouse feel – there are even two drag racing cars on the roof, and the interior is covered in number plates, neon signs, and other automotive relics.

A renovated convenience store, it was opened last June by Ron Metzger. A cheerful, moustachioed, baseball-cap wearing chap in his early 60s, this is his passion project after decades of running his own flooring company.

"I just love Route 66," he says; "I love to make other people aware of its history. I think the route's becoming popular again because people like to visit the past, and relive their parents', or grandparents', memories."

The next morning, we visit a couple of important cultural and political sites. The Dana Thomas House (dana-thomas.org, suggested donation $10) is a prime early 20th century example of the fine architecture of Frank Lloyd Wright, all graphic lines, airy spaces and nature motifs.

Afterwards, we check out the fascinating and engaging Abraham Lincoln Presidential Museum (alplm.org; tickets $15/£12), which charts his life from pre- to post-presidency.

Alton, close to the border with Missouri, is our final stop; and where Illinois' portion of the route ends, too. We check in to the fabulously Southern-gothic-looking Beall Mansion (beallmansion.com; rooms from $119pn), where eccentric owner, Jim, greets us in full white tie and morning coat.
Afterwards, we toast our incredible, retro voyage at the Old Bakery Beer Co.

Statue of Abraham Lincoln in Alton, Illinois. Photo / Getty Images
Statue of Abraham Lincoln in Alton, Illinois. Photo / Getty Images

In the foyer is a life-size drawing of a famous Alton resident, Robert Wadlow; he was the world's tallest man, at 2.7m. That's just the kind of quirky feature we've loved encountering on this route; a reminder that nostalgia is alive and well, along with jolly green giants, the Blues Brothers, drive-ins and dives. Route 66, you've been a blast.

GETTING THERE
Fly direct from Auckland to Chicago with Air New Zealand from $1485. hot.co.nz/usa
DETAILS
visittheusa.com