I mentioned before that our reason for towing the Airstream to Chicago was to get a little work done on our backup camera setup. I’ve been working with Mid-City Engineering, the company that sells the module we’ve been using since 2009. This mod allows me to see the view from the Airstream’s backup camera on the dashboard of the Mercedes GL350.

We had some trouble getting the mod to work in the new GL, and I finally decided to brave the inner city and visit Mid-City in person. This took some planning, as their shop is located off an alley and there isn’t much space to maneuver a 30-foot trailer.

(The red arrow above shows the approximate position of the Airstream.) The only way in was via what is optimistically called Elizabeth Street. That turned out to be the easy part.

The guys at Mid-City fixed us up with a new camera on the Airstream (the existing one was dead for unknown reasons). However, we had to wait until 6:30 for the new camera to arrive at the shop, and so by the time the work was done it was getting dark. Plus, I needed to fuel up the GL and that was never going to work at any of the local gas stations with the trailer in tow.

To help out, the Mid-City guys left all the gates unlocked for us based on our promise to lock everything up when we left. They went home around 7:30, leaving us alone in the dark alleyway.

The owner offered to let us spend the night there, but we decided to head back to the truck lot downtown. So, I unhitched the GL from the Airstream and very carefully maneuvered the car around the building to go get fuel. If you look closely at the satellite view above you might think there’s no road around the northeast side of the building, and you’d be right. There is just barely space to get a car around the perimeter, inches from the brick building and chain link fences. It took me a few minutes to clear all the obstacles.

That still wasn’t the hard part.  Coming back, I had to perform the same maneuver in the dark, backwards because the car needed to arrive in position to hitch up again. That took a bit more sweat and care.

And yet the biggest challenge was yet to come.

Once hitched, the first step was to carefully back the Airstream onto N Elizabeth Street again, and then go forward (southeast).  We couldn’t turn right onto W Walton Street due to cars parked everywhere, so the only escape was down N Elizabeth.  On the satellite image this looked easy, but it turns out that at night the residents park on both sides of the street, leaving only a narrow single lane down the middle for traffic to pass.

That single lane would be no problem for, say, a Mini Cooper.  It was nerve-wrackingly tight for the big Mercedes GL, and seemingly impossible for the Airstream, which is 8.5 feet wide.  Still, I swallowed hard and decided to go for it, knowing that if we got stuck I’d have to back up—and that might be worse.

I wish I had photos, but you know how it is in the moment of crisis. There was a dim light from some streetlamps, and cars parked crazily along the curbs. We literally inched the Airstream forward with Eleanor hanging out the passenger window to look down the side as the Airstream squeezed past parked cars. Our progress was glacial. At many points we cleared cars by about an inch.

At several points I stopped the rig entirely to see if we were completely screwed. A local in his car behind us began honking, frustrated at having to wait a few minutes for this aluminum behemoth to clear his street. That always adds to the fun but I’ve learned not to let people rush me so I ignored the honking.

Finally, we reached a point about 3/4 of the way down the block where there was simply no possibility of getting through—the cars were parked too far from the curbs and we just couldn’t fit between them.

I jumped out of the GL, prepared to go negotiate with the local driver behind us. You can imagine how that would have gone.  ME: “Uh, we can’t fit. You’ll have to back up the alley or we’ll be here all night.”   DRIVER:  “!@$@#$!#$ you, tourist @#$#@%”

But before that happened, Eleanor began folding the side mirrors of the cars parked along the street. Those inches made the difference, and I was able to creep the Airstream past the final cars, inch by inch, without clipping anything.

You can imagine our relief when we finally cleared the block and began working our way back to the highway.  It’s a great feeling to have survived an ordeal like that.  All seemed well as we rolled down the entrance ramp to I-90/94 … and then Eleanor said,

Did we lock the gate?

Of course in all the excitement we forgot about the gate.  So we took the first exit, maneuvered our rig through the streets again, but this time did NOT go down the Elizabeth Street alley.  I pulled over to the side of a larger road with the flashers on, and Eleanor ran down the alley to lock the gate.

Later, set up again in our space at the truck lot, life seemed very peaceful in comparison. Sure, there was still lots of loud activity around us and we had to run the fans all night for white noise, but the roominess of the truck lot felt pretty good after our alley experiences. Plus, the weather had changed for the better and we had a free day in Chicago to look forward to.

As much as this shortened my probable lifespan I have to admit it was fun to face the challenge.  Still, little nightmares like this don’t have to be part of the game for most people.  Recreational towing is supposed to be fun. If you would prefer to avoid premature graying I’ll recommend staying off the side streets and alleys of cities.