The Chicago rider’s calendar isn’t counted in years as much as in seasons. Rather than months, we mark the passage of the season from event to event. It’s weeks counted from one Pints & Pistons to another, months from one Moto Monday at Five Star to another, or so many annual events that we look forward to each year. One of those events is the Distinguished Gentleman’s Ride.


Started in Australia, the DGR began with the photo above: Don Draper on a motorcycle. It then evolved into an international ride raising awareness and money for prostate cancer research. Besides the dapper duds, what makes the DGR unique amongst moto events is that it happens on the same day all over the world.

With my shirt pressed, my vest on, my tie tied and my Bonneville growling underneath me, I headed for Twisted Spoke to attend my very first DGR. I arrived just before the group was set to take off, and the streets around Grand and Ogden were teaming with well-dressed riders. Bikes ranging from small scooters to large motorcycles were lined up everywhere in sight, and in every nook and cranny of marginally legal parking spaces around Twisted Spoke.

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Because Twisted Spoke is a pretty busy intersection, the plan for the ride was to head out from there in as orderly a fashion as we could muster, then actually regroup at Motoworks before departing for the ride proper, which would end near Isle of Man.

Each year the DGR has gotten bigger and bigger. This year in Chicago we saw the better part of 300 bikes turn up in their dapper best. There was a real feeling of excitement in the air. Best of all though, it was a group of friends and friends-of-friends. No sooner had I turned up, I ran into multiple members of the Motoworks crew. I even spotted Johnny making his way through the crowd.

As the bikes started to rumble to life, I pealed off separately to get ahead of the group and watch everyone come in to Motoworks en mass. The group did not disappoint as it arrived. There was no ignoring the parade as it rumbled up Western and filled every spare inch of parking around the shop. We hung out for about half an hour, swapping war stories and looking at each other’s bikes and each other’s wardrobe.

Our fearless leaders gathered us up for a quick level-set before we took off on the ride proper. Basically, stay together and leave room for our escort riders who would be helping us glide more easily through Chicago traffic. With those points of order established, there was nothing left but the ride itself.

Bikes fired up once again. In the small quarters of Western and 19th, the noise was amazing. You were lucky if you could make out the note of your own machine. With Bob at our front on his Vespa, the group snaked out on to Western and the ride was on! I found myself about a dozen people back, so I had a great view of the front of the ride, while at least two hundred other dapper riders followed behind.

If you’ve never been on a big group ride like this, you don’t know what you’re missing. It’s about being a squadron of riders working together. There’s a pride involved. Pride in your group. Pride in your bike. Add to that the DGR’s opportunity to have pride in your outfit and pride in your city. That many riders working together always makes me think of the Royal Air Force during The Blitz. Squadrons of planes scrambled to defend queen and country, each piloted by an individual who had chosen to embrace the danger and the thrill of their mission. Today’s peacetime mission was to get out there and ride through Chicago for the sake of prostate cancer research.

At each stop along the way, the group would bunch up and the combined notes of our exhausts would blend into a symphony of throbbing motorcycle thunder. I could feel the other tones rippling through my own exhaust as the harmonics came and went. I couldn’t resist the urge to crack my own throttle simply to hear which note was mine. That activity was contagious.

Along the way our parade of bikes was met with the occasional sneer, but for the most part, Chicago was excited to see us. We got waves from people of all ages and excited honks from cars and other bikes along the way. It was obvious we were no outlaw biker gang. We weren’t the Sons of Anarchy. We were the Sons and Daughters of Chivalry.

We arrived in the general vicinity of Isle of Man and began filing into all the parking spaces we could find. Unfortunately, we found IOM closed for construction. What does an enthusiastic group of riders do without a plan? Head for the nearest bar, obviously.

The group splintered at this point, but that was fine. We’d had a glorious ride on a beautiful day. Now it was time to spend some time enjoying the rest of that day. Most of the Motoworks crew headed for Floyd’s Pub, where we enjoyed food, beverages and each other. The group was split, half inside watching the Bears game, the other half out in the beautiful autumn weather. There may be a better way to spend a Sunday, but I can’t think of it.

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Today was a reminder of the absolute best aspects of riding. A great ride, amazing weather, a good cause, wonderful company and all of it on two wheels in one of the greatest cities in the world. Seriously, how do you beat that?

Did you miss it? I missed the DGR in previous years. I won’t be missing it again.