On Route 66

2637 Miles from Chicago to Los Angeles by Bicycle


Tuesday, 05 May (Day 1)

Woodstock, Illinois to Carol Stream, Illinois

Off to a good start. The weather was near perfect – cloudy but no rain, temperature in the low fifties, a slight wind at my back most of the day. And the 44.7 miles from home to my sister Jo Ann’s house in Carol Stream was almost entirely on asphalt or crushed limestone rail-to-trail bike trails, so the ride was flat and fast.

Ready to roll.

The first ten miles on the Ridgefield Trace trail from Woodstock to Crystal Lake were very familiar. I’ve ridden that trail so many times that I can almost do it in my sleep. Then it was over a few side streets through Crystal Lake and onto the Prairie Trail where I turned south. The Prairie Trail joins the Fox River Trail near Algonquin and, as the name implies, runs along the Fox River and through the many small cities and towns that lie along it’s banks. At South Elgin, I left the Fox River Trail and connected to one of the oldest rail-to-trail trails in the country, the Prairie Path. I rode the Prairie Path all the way to Carol Stream’s bike path system and a short 2 ½ mile ride to my sister’s house, where I’d spent the night. All in all, 5 hours of fairly easy riding. When I pulled into Jo Ann’s driveway just before 3 PM, my legs and butt were only a little sore and, more importantly, it looked as if I had avoided the first day jinx which seems to plague all my adventures.

On the Ridgefield Trace. All my adventures begin with this ride.
The Prairie Trail to Algonquin.
Took a short break near this stream in one of the many parks along the Fox River Trail.
The Fox River.
The Fox River Dam in Elgin. Illinois
Marsh preserves along the Prairie Path

If you’ve read my previous adventure blogs and journals, you know that some minor catastrophe always seems to occur on the first day of my adventures. A broken seat on the first day of my ride to Yellowstone in 2023, three flat tires in the space of forty minutes on the first day of my ride around Lake Michigan in 2024, and backing a canoe-ladened car into a ditch near the boat ramp on the first day of my Lower Mississippi River paddle in 2025.

So why would this year be different? Something was going to happen. And something did.

No sooner than a few short minutes after bringing my bike into my sister’s house and giving her a hug, that the kick stand on the bike sheared off, sending the heavily-loaded bike onto it’s side with a crash! Visions of broken spokes, misaligned derailleurs, busted panniers brackets, and a myriad of other likely adventure-delaying catastrophes raced through my head! But my luck was with me, and aside from the broke kick-stand and two misaligned mirrors, nothing appeared to be damaged.

So, resigning myself to the idea of now having to lean my bike against some support or other for the remainder of the trip, I sat down to a delicious lasagna dinner with Jo Ann and another of my sisters who drove out to join us, Cherrie. And it was over dinner that the idea of how to repair the kick stand occurred to us. Anyway, long story short, we found an old length of electrical conduit pipe in Jo Ann’s garage, cut it down to size, and slipped it over the bit of kick-stand still attached to the bike. A little drilling and a couple machine screws later, we had ‘McGiver’ed” a new kick-stand! I’m not sure how long it’ll hold up, but for now it looks like it might last long enough to do in a pinch.

Repaired kickstand.

After that job well done, we wrapped up the day with a slice of lemon-and-cream pie to early-celebrate my birthday. And I was off to bed. My muscles may not have been sore after today’s ride, but I was certainly tired. It’s a short 36 miles or so to tomorrow’s destination, Joliet, Illinois. At Joliet, I turn southwest towards St. Louis and begin my ride down old US 66.

Weather is forecast to be even better tomorrow than today.



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