Chicago is the country’s third largest city, yet it can still feel really small and close sometimes. The bike community here can feel especially intimate when any of us shows up to one of the weekly or monthly bike events. We’ll see old friends, familiar bikes and newcomers alike, but at any one event, we don’t often get a sense for just how big and how vibrant the Chicago motorcycle and scooter scene really is. That is, until something like the Distinguished Gentleman’s Ride.

Last Sunday the scene was packed with dapper ladies and gentlemen dressed in their fancy finest for what’s become one of the year’s biggest perennial events. Bikes of all types, sizes and vintage began rolling in at Cobra Lounge bright and early at 9:00 AM. Skies were foggy, but the day’s forecast promised we’d stay dry. Gray skies or not, bikes and riders began pouring in and lining Fulton St in front of All Rise Brewing. The breakfast buffet was in full swing, and rumors of a few breakfast beers can be neither confirmed nor denied.


Upon arrival, each bike and rider first passed through the Motoworks Chicago photo tent, where photog Matthew Driscoll snapped their dapper photo. With hundreds of people turning up in the end, Matt snapped a load of photos, which you can see over on Facebook. There are 357 entry photos in total, but we’d wager there were plenty of bikes and riders who opted out of the photo, if only because they arrived from the other direction.

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Mixed with the silly energy of everyone in all their dapper best, the ride hadn’t even begun, yet it seemed like everyone was having a blast. Before 10:00 AM rolled around, the street in front of All Rise was swelling with bikes. We began parking them up the center of the street, which given the venue, couldn’t help but remind us a bit of Motoblot. It wasn’t long before bikes were being parked in every last nook, cranny and side lot in the immediate area.

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The Motoworks crew, the Chicago chapter of the 59 Club and Ton Up Chicago club were moving through the crowd, making sure everyone knew where they needed to be and making everyone feel welcome. Johnny, looking extra sharp in his tux, directed a lot of traffic through the photo booth while our own Anna made sure people knew how to get their photo afterwards. Then of course there was Larry Fletcher and his signature grin, operating as master of ceremonies.

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The sheer variety of bikes and outfits in attendance was highly entertaining. The DGR started in Australia as a celebration of formal fashion, classic bikes and modern bikes that look like classic bikes. As the event has grown, the enthusiasm and desire to participate has exploded worldwide. Add to that the charity component raising money for prostate cancer research, and people have come out of the woodwork to participate.

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In Chicago, classic style and vintage bikes were everywhere, piloted by men and women in their dapper best. Yet there were also plenty of properly modern and off-category machines as well, which if you ask me, only added to the richness and energy of the event. There’s something extra terrific about the contrast of bike and rider when the rider is dressed to the nines, but the motorcycle was something outside the typical retro design. The rougher, weirder or more modern the bike, the more its well-dressed rider seemed to stand out against it. Seeing as it was all for the good cause of charitable giving, community and the sheer fun of getting together, no one was out of place. We were united in a common generosity of purpose, and a common love of all things two wheel. It’s our hope that for next year, the global organizers of the DGR will abandon their Style Guide and embrace what is, for us anyway, the real soul of the event: getting dressed up and riding bikes for a good cause. To everyone who ignored the style guide and rode anyway, we love that you came.


The ride itself was scheduled to kick off at 11:00 AM. At Larry’s word, the crowd began to spread to the hundreds of bikes that now littered Fulton St. One by one, these machines fired to life and began to form the body of the ride. This rumbling snake of men, women and machines would slide its way down Ashland Ave, then head east on Jackson toward Chicago’s iconic Lakeshore Drive. In the original ride plan, the group was going to head south to the Museum of Science and Industry. Unfortunately, we had to edit that part of the ride out due to marathon-related road closures. So instead, the group would parade through Chicago’s downtown loop and head north on Lakeshore instead. Our final destination was the Holiday Club on Chicago’s north side.

The group departed together in a fluid, orderly fashion. It was really something to see so many bikes and riders assemble and ride away together in such a short amount of time. At a leisurely pace, the group made its way across the heart of downtown Chicago. With around 400 bikes, we were hard to miss. Yet for all the low-level mayhem our little parade caused, the response we got from our unwitting spectators was enormous. Car drivers honked horns in delight. Kids jumped up and down. Adults waved and cheered us on. While the general public might not have known exactly what was going on, they could certainly tell it was something special.


The group made the turn onto Lakeshore drive and positively took it over. We were a sight to behold: all rumble and pomp, speed and style. While the ride itself was relatively short, it was rich. Soon we were off of Lakeshore Drive and making our way to the Holiday Club. Once there, we lined the bikes up in four directions around the intersection of Sheridan and Irving Park. With the ride done, now it was time to party.

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The atmosphere was no less electric than before we’d left. With the energy of the ride coursing through us, the group unwound at Holiday club, sharing meals drinks and each other’s fine company. Even parked our parade attracted no shortage of attention, and the mob of well-dressed riders overflowing out of the Holiday Club left the locals scratching their heads in the best possible way. This was no ordinary biker gang.

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As these things do, the 2015 Chicago edition of the Distinguished Gentleman’s Ride came to a close. Each rider went their separate ways, with small bands pealing off for after events, football games and all the other trappings of a autumn Sunday afternoon. Once again, the DGR had proven itself a can’t miss event on the yearly Chicago calendar, and I’d wager that all across the city, people were already thinking “what shall I wear next year?”

Huge thanks to Larry and Steel Toe Press, to the 59 Club, to Ton Up Chicago, to All Rise Brewing and Holiday Club for hosting, to Triumph for sponsoring, to the global DGR team for coming up with this wild idea, and especially to everyone who came out in their dapper best and made this year’s DGR what it was.

Also, special thanks to Matthew Driscoll, Alex Hawn, Cat Pham and Seth Kane for contributing photography for this post.

Gallery: The 2015 Chicago Distinguished Gentleman’s Ride