Part 1 — Chicago to southern Illinois

As I mentioned at the end of my last regular column, I’m now on a road trip with two of my cousins, driving across country on Route 66, from Chicago to Los Angeles.  One of the cousins recently bought a 1976 Cadillac Eldorado just for this trip, and instead of writing my regular columns, I’m going to post a series of reports from the road.  I’ll also put the entries together once I get home, and post them and some pictures from the trip, probably on my page at

These feel a little out of my wheelhouse, and they might not be everyone’s cup of tea.  They won’t have a lot of political mockery or my usual musings and nonsense.  So if you are not interested in these entries, I will be back writing my regular snarky columns after the trip, so I hope you’ll rejoin me then.

For the rest of you, here’s the first entry:    

Day 1: Saturday, May 1st.  I flew up to Chicago and the guys picked me up, and we started our trip from the spot where Route 66 begins, a few blocks off of Lake Shore Drive.  We spent the first day driving almost the length of my old home state of Illinois, stopping for the night a little south of Springfield.

First, a few words about the car.

It brought me back to my childhood in a way that few things can do.  It’s 45 years old, and as soon as I sat in it, a thousand memories flooded back: the AM/FM radio with 5 buttons to pre-set your favorite channels, the skinny steering wheel, the undersized side mirrors and the over-sized everything else.  Even the smell of an old car, and riding in the backseat for much of the time (as we traded off driving duties).

The beast is white with red interior, and it’s nearly 20 feet long.  It gets about 10 mpg, it floats down the road, and there’s a lot of play in that skinny steering wheel before a turn starts.  And then it’s like turning a battleship. 

It obviously comes from a different age, one that wasn’t nearly as concerned with safety as our own (for good, and for ill).  There is an ashtray in the front below the dash, and one on each side in the rear, and all three of them have their own built-in lighters.  All of the seatbelts are lap-belts only, which ensures that if we hit something, we will all bend forward violently at the waist, jack-knifing into the airbag-less dashboard. 

So, smoke ‘em if you’ve got ‘em, I guess.  And conveniently, all three of us could light a cigarette simultaneously if we wanted to.  If any of us smoked.

And this particular car is no pristine, pampered, showroom-model.  The speedometer, cruise control and a.c. are broken, and in heavy rain, with the convertible top up, a few refreshing drops of water seep in and around, and drip onto the driver and front seat passenger.  Though the electric windows work, raising the two small, rear windows is a two-man job: while one sits in the driver’s seat pushing the switch to raise the window, another grips the top of the rising window and applies just enough pressure to help it slide up into position.

But we cousins are cautiously optimistic, Midwestern-raised Ameri-CANS, not nervous little hypochondriacs who insist on things like functioning airbags, or three-point seatbelts, or dashboards that are not made of skull-crackingly hard materials. 

Sure, we’ve got no cruise control.  Did our great-grandparents’ horses have cruise control?  (Seriously, I have no idea what kind of standard equipment package a pony used to come with.   But unless I’m mistaken, they each only came with one horse-power!  So I’m going to guess that they very rarely had cruise control.)

Sure, when it rains outside, it rains a little inside.  Did the old-timers’ covered wagons provide a perfectly dry interior during rainstorms?

Sure, we never have any idea how fast we’re going.  But think of the glorious, ethically satisfying opportunity of having a cop pull us over and ask if we know how much he clocked us doing, and being able to look him dead in the eye and say, “As God is my witness, I have no idea.”   

Also, we’ve implemented a work-around for that.  (Again: Ameri-CAN.)  One of us sets up his Tom-Tom – whatever that is – and it shows a speed on it.  Sure, the screen is often nearly unreadable in direct sunlight with the top down, and we have to keep glancing down to check it, anyway.  But: neither Lewis nor Clark, nor Paul Revere, nor Grant nor Sherman, nor any of the 49ers had speedometer-equipped horses. 

And I’m pretty sure they all made it to the Santa Monica pier at some point.  Though I’m not a history major, so don’t quote me on that. 

Anyway, the car has her flaws, as do we all.  But she’s a big, old American beauty, and we receive thumbs up and compliments and questions about the car wherever we’ve gone so far.  And the bottom-line is that driving Route 66 for over two-thousand miles in an airbag equipped, modern generic-mobile would still be fun. 

But not as much fun as driving it in a car that might not make it there and back, but will look cool doing it!

So Day 1 featured fine, cool, sunny weather, and we went through dozens of small towns that feel like home to us, since all three of us grew up amongst them.  We had lunch at the little restaurant beside the Gemini Giant in Wilmington, and saw the solemn columns of identical gravestones lining the gently rolling hills of the Lincoln National Cemetery.  We saw some Blues Brothers statues and vintage cop cars in Joliet, and an iconic downtown with murals and a Route 66 museum in Pontiac. 

My favorite moment of the day came in Normal, IL, when we went into a restored old store and talked to the sweet older lady behind the counter.  Cousin #1 (I’m withholding their names to protect the guilty) saw a very old photo of a group of farm kids posing in front of a very old tractor, and he said, “I guess all of those kids are dead  and gone.”

And the sweet older lady pointed to a sweet little girl in the picture and said, “That’s me, there.” 

We will never stop mocking my cousin for this.

Farther south, we saw the first of a series of kitschy, oversized “Largest X in the world” oddities.  This time it was an enormous, covered wagon made of steel, with an enormous Abe Lincoln sitting up front.

We made it through Springfield as the sun was starting to set, so we had a satisfying BBQ supper (Surprise! None of us are vegans.) and stopped for the night near the southern tip of Illinois.

I hope to post these nearly daily and get caught up on our trip  — if any of you are still interested! – but without a strict itinerary, a little is still left up to chance.  But I’ll do my best.

Next up: from southern Illinois to Joplin, Missouri

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