It sounds obvious when you say it out loud, but the best part about putting on events through the shop is that people show up. We’ll send out an email that something is happening and moto fans from across the area will turn up and take part. That’s remarkable, and we really appreciate it. Whatever we’re up to, it’s just more fun when we’ve got friends along.

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Last Sunday was the last Sunday in June, which meant it was time for the monthly meeting of Coffee & Classics in Winnetka, just north of Chicago. While typically a car-centric event, this month C&C was featuring an iconic vintage motorcycle brand. Great Britain’s own Vincent Motorcycles would be the center of June’s event, and Motoworks had been invited to bring as many moto fans as we could to participate in the event. The Chicago community did not disappoint. Around 30 bikes turned up for the 8:00 departure time — damn near heroic for a Sunday morning.

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Our group was a mix of modern and classic bikes, but at the head of our moto parade was a particularly interesting classic BMW. Piloted by our own Johnny Scheff, I rode “monkey” in this gorgeous /2 BMW sidecar rig with R90/6 drive train and other details. The sidecar itself was even a rare special edition unit badged from the factory as a BMW. At 6’3″, I wouldn’t say I had a ton of room in the sidecar, but I was actually very comfortable. As we pulled away from Motoworks and headed toward Hwy 55, I was pleasantly surprised just how well this classic machine performed and handled with a whole lot of man onboard. In fact, Johnny pointed out that these sidecar rigs actually perform better when they’ve got some work to do.

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My vantage point from the sidecar was as novel as it was entertaining. Imagine all the freedom and visceral excitement of riding your motorcycle, then imagine doing it about a foot off the ground. I’m not going to lie to you, Marge, it was hilarious to zoom by cars and bikes alike in that BMW sidecar. Better still was the parade of other motorcycles Johnny and I had in our wake. Everybody seemed to be having a good time, but I definitely had the best seat in the house.

We cruised up Lakeshore Drive, repeating the route we’d explored the week before on Vespas. We definitely got some funny looks as we cruised by, with me looking up at the other motorists in their driver’s seats. The R90/6 engine purred and pulled no problem. We’d taken this sidecar rig out on this Sunday ride for more than just giggles. We’ve got a customer very serious about purchasing this rather unique and valuable machine and since we’d only just recently taken it in ourselves, this trip up to Coffee & Classics was going to serve as a quality control exercise. Johnny was noting loose fairing bolts and a low idle speed as we went. On the uneven bits of Lakeshore Drive, we were doing a literal shake-down ride.

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Turning onto Sheridan Rd, we didn’t make it far into Evanston before we started seeing other bikes and cars that were surely headed to Winnetka for C&C. When you see a Porsche Speedster replica chasing an E-Type Jaguar, you know you’re headed in the right direction. We even picked up a couple classic BMWs along the way.

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Arriving at Cafe Aroma, the event organizers had quartered off a small section of street for our motorcycle group to park. On the opposite corner, a half dozen Vincent motorcycles were already on display, like a cornerstone to the event and its goings on. The event spilled out of the intersection in three directions, with bikes at its center, and an interesting, eclectic mix of exotic vehicles radiating up the surrounding streets about a block in each direction.

I’ve been to a lot of motor-oriented events and festivals, but this was my first time to Coffee & Classics. These events all have their own tempo, and Coffee & Classics had this great, low-key vibe. There was no attempt to manufacture extra, unneeded atmosphere. The interesting vehicles and their owners was all the event needed. No food truck. No beer booth. No merch table. No drone of house music put on by the local radio station. The only noise was the occasional vintage car burbling by — a much better soundtrack if you ask me.

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The centerpiece of the event, the Chicago chapter of the Vincent Owners Club, not only showed up in force, but according to FuelFed set an AMA record for the most Vincent motorcycles in one place in America. Not bad for a sleepy little event in the Northern ‘burbs, eh? The Vincent brand is well known, but rarely scene, We all know the shape of that iconic, squat v-twin engine, but you don’t see them that often. This Coffee & Classics event was a really interesting opportunity to not just see a Vincent in the metal, but actually see them go and hear them run. From a sound standpoint, there was a remarkable similarity to the civilized grumble of an old BMW airhead. Not quite the same, but similar — definitely not the sloppy, droning chugga-chugga of most v-twins we hear on the road today. Cool stuff, and a great group of owners — guys who got into these old bikes “back before it was cool” as Johnny put it.

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Seeing so much interesting iron in one place sheds light on a really interesting segment of motor enthusiasm: the collector. Bikes like the Vincent are becoming serious collector’s items, with significant values to go along with them. Yet at Coffee & Classics, they were in extremely good company amongst the vintage Jaguars, Ferraris and BMWs. I overheard several owners swapping the stories of their machines. Several started along the lines of “Well, I got the bug back in ’94 and really wanted something interesting…” I love that notion of “the bug” — something I know all too well in my own garage. I’m not collecting Vincents or Jaguars, but I can appreciate the obsessive impulse — the drive toward an interesting machine. Maybe it’s taking something newer and customizing it. Or maybe it’s the care and feeding of a properly collectable machine. Either way, I can really appreciate the care-taking involved. It’s time and energy well spent, and it’s the best aspect of Coffee & Classics if you ask me.

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It’s also worth pointing out that not everything at Coffee & Classics was some sort of rarified, 6-figure collector’s car. There were plenty of more accessible machines. From classic Mini Coopers, to MGs, to Triumphs (cars and bikes), to vintage BMWs (cars and bikes) — there was plenty of cool metal within the reach of mere mortals. Sure, there was also more than one E-Type Jag, a Benz 300SL convertible, and an Aston Martin DB4, but it’s the mix of things that makes it the most interesting, I think. Having all the bikes mixed in was a great addition too. Hopefully the organizers feature more moto brands in the future.

Though we all arrived together, the group dispersed on its own. When the time came for Johnny and I to roll back, we mounted back up and rather conspicuously exited Coffee & Classics. While I don’t know when I’ll next arrive via sidecar, I know for sure this won’t be my last time to Coffee & Classics. If you haven’t been, I highly recommend it.

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Rolling back south, Johnny and I flew down Lakeshore Drive to lower Wacker, just as we had on Vespas a Sunday ago. Yet this time we didn’t get far. It was Pride week in Chicago, and the parade had us diverted. No big deal. We both chuckled at the irony — a couple of dudes in the most conspicuous vehicle available cruising the surface streets of the Loop during Pride. No big deal. We diverted through the relatively relaxed Sunday afternoon streets of downtown Chicago, getting stares from people as they crossed the street in front of us at stop lights, and waves from groups of women tourists. There’s no blending in while riding a vintage BMW sidecar rig. Forget about it.

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Like our Vespa trek the week before, cruising the town on an interesting motorcycle was a reminder of just how much fun there is to be had when you combine good people and an interesting machine. Coffee & Classics had only sweetened the deal. We would have had plenty of fun just bombing the sidecar up to the North Shore and back.

As we arrived back at the shop, Johnny compiled his fix list for the BMW. The idle was a little low. It could stand a fresh balance between the carbs. A handful of bolts needed shoring up or replacing in the fairing assembly. At its core though, the sidecar rig had been brilliant. The BMW was comfortable, quick and just a joy to ride. Its new owner is going to love it. I’m more than a little jealous, to tell the truth. My first exposure to a sidecar had definitely given me an itch I’ll need to scratch someday. In the meantime, I’ll be watching my inbox for the next Motoworks riding adventure. You do get Johnny’s event emails, right?