For a sign with so much significance, it’s not that impressive; small, brown and white, and stuck way up on a pole on the corner of 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, that connected America’s gritty east to its sunny west officially opened 94 years ago, in April 1926. It’s inspired — or been seen in — movies, songs, TV shows, and become the shorthand for a certain type of nostalgic, kitsch Americana, instantly recognised around the world.
Oddly, Route 66 is not one continuous road; its creation was, essentially, the linking together of smaller, existing ones. Technically decommissioned in 1986, it’s no longer maintained by the US Highway System, and as a result, parts of it aren’t driveable. But the start and state of Illinois still has a good 480km, ideal for a weekend trip.
Driving out of Chicago — 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 still on track, and before too long we pull up at the Old Joliet Prison. Built-in 1858 and in use until 2002, it featured in cult movie The Blues Brothers and offers $20 tours.
Back in daylight, and 30km on, rounding a bend in the road by the tiny town of Wilmington, looms a strange sight.
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 opened in 1956 and closed in 2007.
In 2017, Holly Barker and Tully Garrett bought the building — and the Giant — and restored it.
“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. 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. 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.
Later that afternoon, we reach Springfield, Illinois’ state capital — where Abraham Lincoln lived for 24 years — and check in to the Inn at 835, before making our way to Motorheads Bar and Grill (66motorheads.com) just off the route, for dinner. It has a classic roadhouse feel with two drag racing cars on the roof, and the interior is covered in automotive relics. The next morning, we visit the engaging Abraham Lincoln Presidential Museum.
Alton, close to the border with Missouri, is our final stop; and where Illinois’ portion of the route ends. We check in to the Southern-gothic-looking Beall Mansion where eccentric owner, Jim, greets us in full white tie and morning coat.
Afterwards, we toast our retro voyage at the Old Bakery Beer Co.
In the foyer is a life-size drawing of 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. Route 66, you’ve been a blast.