[A nod here to my once-and-future riding partner—and the very first subscriber to this blog—Jon Scott, who blogged his cycling tour of the lower 48 last summer (https://www.shiftinggears57.com/), and who frequently used song lyrics for the titles of his posts.]
COVID KO’ed the Grand Illinois Bike Tour in 2020. When the event returned in 2021, the route began in Litchfield, dropped down to O’Fallon, then Edwardsville, then a day trip across the Mississippi to the Arch, then back across to Alton, then return to Litchfield. We spent a significant amount of time on the very nice rails-to-trails bike paths in Madison County. Outside Hamel, IL (the horseradish capital of the world), at one of the Tour’s rest stops, we encountered a cyclist who had come all the way from Los Angeles, following the approximate path of Route 66 to Chicago. He was within a few days of completing a very, very long solo ride. I was fascinated… and entirely intimidated by the thought of such an undertaking.
But then, in 2022, two things happened: first, in May, I reconnected after a 30-year hiatus with the aforementioned Jon Scott, when our paths crossed coincidentally in Alabama of all places, and started tracking his blog as he biked his way around the US. Second, in June, the GIBT shifted north, and a good portion of the ride included the Route 66 corridor (Bloomington-Pontiac-Dwight), which got me feeling a little less intimidated and a little more fascinated by the thought of biking the “Mother Road.” By the time I saw Jon again in July, and joined him for a few days of riding between Illinois and Wisconsin, a seed was starting to take root: I was going to ride Route 66, albeit not in a single trip. I would bite it off in sequential chunks–the way that some people hike the Appalachian or Pacific Crest Trails. Cycling west from Chicago to LA, my goal would be to reach the Santa Monica Pier by the numerologically significant date of my 66th birthday in August of 2026.
The first leg, Chicago to St. Louis, starts tomorrow. I’m taking the train to Chicago, and meeting Jon, who’s flying into Midway to join me for this segment… and hopefully several more along the way. We’re planning to start riding almost as soon as he gets his bike out out of the box and gets the pedals screwed on. The challenge isn’t just the daily distance; it’s getting the daily distance to match up with the availability of decent but inexpensive hotels. And, right off the bat, there aren’t any decent but inexpensive hotels in Chicago on a Saturday night, so we’re going to get outside the city limits.
If all goes well, we’ll be in Pontiac or Dwight by Sunday night, Bloomington on Monday, and in my own house in Springfield on Tuesday. That gives us two days to get to STL before Jon’s flight home on Friday morning. Totally do-able (although Jon’s been following the prevailing winds more closely than I have, and tailwinds seem unlikely.)
I’ll be posting our progress, and Jon’s reactivated his own blog from last summer. Come along for the ride, and get your kicks.
Rideworthy 