Gettin’ some Kicks: Cycling Route 66 in Illinois

Everyone should drive on Route 66 at some point in their life. You don’t need to take it the whole way from Chicago to LA to get a flavour of its iconic status and enjoy the touristy fun. Especially if you love 50s kitsch, burgers and ice cream, giant statues and bumpy roads. The route is crammed full of things to stop and look at, some good, some not so good, some bizarre. Even four days by bike is enough to see why so many people flock to the USA to drive on a route that doesn’t really even exist anymore. 

We didn’t start in Chicago – riding through miles of city suburbs isn’t that appealing – so joined “historic Route 66” as it is officially called just south of the city. This day marked quite a change in the trip, as it was the first time we had ridden for a whole day on busier roads. Straight away the noise of the interstate that runs alongside the route was noticeable after being accustomed to peaceful bike paths. The heat had also been cranked up a few notches, to the point where sweat dripped from various bodily locations for the first time. The scenery opened out and we could see for miles and miles. I’m not sure where the mid-west officially starts but life felt different in more than one way from this point on.


Day 1 highlights (or lowlights, everyone is entitled to their own interpretation) included a large spaceman holding a large fish; burgers and milkshake in a diner that had comedy mirrors and more Elvis memorabilia than you think could fit in one building; a small jail; a restored train dining car; and a couple of restored gas stations where the women who worked there could not have been more different in their welcome. First up was a Route 66 enthusiast who complemented Debs on her shorts (yes they are Lycra) more than once, and then when she insisted on taking a photo of both of us in an old car only managed to turn the camera off rather than take a photo, despite having very clear instructions to press the large button to shoot. We took the first opportunity to escape (after at least 20 minutes) without even making use of the toilet. Further down the road her oppositional counterpart barely looked up when we entered, and definitely did not have any drinking water for us. Pick your Route 66 attractions carefully.


Our final stop of the day was Pontiac, home of many Route 66 murals (including the largest one in Illinois) and a museum that couldn’t have fitted more old stuff in. The main attraction is a VW van owned by Bob Waldmore, a guy who spent most of his life driving Route 66. Such was his iconic status that the makers of Disney Pixar’s “Cars” modelled the character Filmore on him, and initially wanted to name the character Waldmore. The museum has some interesting letters between Bob and Pixar as to explain why this didn’t actually happen. It’s a good story, google it. It was so hot outside we sat in the museum foyer and ate sweaty cheese sandwiches until they closed. That night we ended up between campsites and were saved by an invitation by a friendly family to sleep in a their trailer (caravan to the Brits).

Day 2 continued in much the same fashion, though without the sunshine which cooled things down a little. More old signs, more old diners, more big things, more museums. And then day 3 too. There’s not much variety. It could get repetitive, but it’s all good fun for a few days. We ate burgers, ice cream and cream pie. It’s fun travelling the route at cycling speed because there is something to stop at every 30-45 minutes to break up the monotony of what is a fairly unexciting road to ride on, often right alongside the interstate. Maybe in a car it would get annoying stopping every ten minutes, I don’t know. Another reason that bikes are best 🙂

The final day riding into St Louis was a short one at only 45 miles but we still made it take all day by stopping for a long bakery breakfast on the way. As we got closer to the end point of our Route 66 adventure, the attractions dried up and we switched to Lewis and Clarke information, the explorers who set out from Missouri to ‘discover and claim the West for America’. We crossed the mighty Mississippi River into Missouri on the old chain of rocks bridge, now closed to cars and famous for having a 22 degree bend in the middle. It had got really hot, and it was hard to believe that just seven days (and 500 miles) previously we had been sat watching it snow from a window in Michigan.


We would follow the Lewis and Clarke route for a few days out of St Louis but first we had to explore the city. Doug and Marta our amazing warm showers hosts met us at the Gateway Arch (gateway to the West of course) and took us on a bike tour of the city. The next day was the most tiring rest day imaginable as we went to the St Louis City Museum. This place bears little resemblance to a museum but is more accurately a huge adventure playground for adults and kids, with pretty much everything made from salvaged material. There’s an old FBI plane to climb through, a school bus perched on the roof top, a large ball-pit, underground caves and mazes of climbing frames made from old industrial factory cast-offs. We spent four hours hauling ourselves through small holes and climbing over things (including small children), to the detriment of our arms the following day. It’s a very cool place. But it’s not a museum. And It’s definitely not a rest day activity.


Before leaving St Louis we just about had time to try some local delicacies. On the way we had already experienced concrete, a frozen yoghurt that does not move when you turn it upside down. Second up was gooey butter cake, a cake that was very gooey and buttery. Finally we went out to Blueberry Hill, a very cool place where Chuck Berry still plays once a month, for burgers. Yes these are everywhere but as a side order we tried deep fried ravioli – though it’s called toasted ravioli for some reason. I prefer it’s abbreviation of T-Rav. Sounds much cooler. And it tastes ok too.



Big thanks to Neil; Theresa and family; Tom, Martha, Alex and the rest of the family; and Doug, Marta and friends.

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