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Motorcyclists ride through downtown Naperville for the Distinguished Gentleman's Ride on Sunday, May 18, 2025. This year the event will be Sunday, May 17. (Thom Higgins)
Motorcyclists ride through downtown Naperville for the Distinguished Gentleman’s Ride on Sunday, May 18, 2025. This year the event will be Sunday, May 17. (Thom Higgins)
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Thousands of motorcyclists donning their most dapper attire will take to the streets around the world Sunday, May 17, to benefit men’s health issues — including here in Naperville.

The annual Distinguished Gentleman’s Ride brings together classic and vintage motorcycle riders to raise money and awareness for men’s mental health and prostate cancer research.

Founded in 2012 in Sydney, Australia, motorbike enthusiast Mark Hawwa was inspired to start the ride after seeing a photo of Don Draper from “Mad Men” astride a classic motorcycle while wearing a suit. After a successful first year, he decided to use the event to raise awareness about prostate cancer. The event is now part of Movember, a national organization dedicated to raising money for and awareness of men’s mental health, prostate cancer and testicular cancer.

Motorcyclists drive down Webster Street in Naperville during the Distinguished Gentleman's Ride on Sunday, May 18, 2025. (Thom Higgins)
Motorcyclists drive down Webster Street in Naperville during the Distinguished Gentleman's Ride on Sunday, May 18, 2025. (Thom Higgins)

This year will see more than 1,000 rides across the globe. Five of them will be in Illinois, including Chicago, Champaign, Springfield and Woodstock in addition to Naperville.

The local event started seven years ago when Sven Davies and a few of his friends held an unofficial ride to the city’s downtown. As he learned more about the Distinguished Gentleman’s Ride, Davies and friend Mark Jacquot decided to make the event official in Naperville.

“We just started doing it and each year it gradually got a little better,” Davies said. “Our first goal was to raise $1,000. The next goal was to raise $5,000. Last year, our goal was to get above $10,000 and this year our goal is 100 bikes and to get over $15,000.”

Naperville hosts the second largest ride in Illinois, drawing attendees from neighboring communities like St. Charles and Aurora. Davies said that last year’s event had so many cyclists that they completely filled the Naperville Township parking lot at the end.

Currently, over 60 people have signed up for this year’s event and more than $13,000 has been raised.

This year the ride will feature two parts: a 14-mile ride and a pop-up event for spectators.

For those participating in the ride, the day starts at 9 a.m. in an area near Ogden Avenue and Washington Street. Bikers will be given coffee and doughnuts before being briefed on safety. From there, Naperville police guide bikers through the route, which goes from Naper Boulevard to 75th Street and through the downtown area before ending at the township lot on Water Street.

Anyone interested in participating must register online at gentlemansride.com/events/united-states/naperville-il. Capacity is limited to 125 cycles.

Riders are encouraged to dress up in bow ties, jackets and vests. Vintage and classic motorcycle bikes are preferred but riders won’t be turned away if they do not have one.

Spectators can view the event by heading down to Water Street in downtown Naperville as early as 10 a.m. American grass roots band Tank and the Beez will perform, and the motorcyclists are expected to arrive between 10:30 and 10:40 a.m.

“What’s going to be really exciting is for those people who are going to be down on Water Street, they’re going to get to see us all come in, park our bikes and will be able to witness a hundred bikes coming into that area, and then get to look at the bikes and talk to the riders and really have a nice time,” Davies said.

A number of vendors will also be present, including local hearing aid company Audionova, the St. Charles Motorcycle Museum and mental health provider The Juniper Center. Aurora-based radio station 95.9 The River will be covering the event.

It’s expected to last until 12:30 p.m. though Davies noted that SixtyFour Wine Bar & Kitchen on Water Street will be open for diners. A portion of the proceeds from noon to 3 p.m. will go to the fundraiser.

cstein@chicagotribune.com