21st Century Harley — A Look Back, A Ride Forward

The idea of a trip to Milwaukee wasn’t something we’d expected in the SHARP calendar, and yet there we were. The city is the home of Harley-Davidson, and though you might not clock that on a normal Thursday afternoon, the rumble of HD Homecoming and its inbound attendees was impossible to miss. With nearly 20,000 motorcycles converging for a weekend of music and motorcycle culture, the annual festivities put on by the brand draw in all kinds — from the seasoned brand-loyal riders, to those just starting to get a sense of what Harley is all about.

Being one of the latter, I set out for Milwaukee for a bit of a peek behind the curtain, so to speak. As a seasoned rider, I knew full well that the archaic lore of Harley riders, gang affiliations, and beyond only painted a small fraction of the picture. It wasn’t hard to spot the stereotypes within the crowd, but it was also refreshing to see a myriad of faces that fell far outside that particular typecasting. Young and old; male, female, and non-binary; people of every creed and colour all rallied at the weekend’s events.

While some were there for the massive outdoor performances of The Offspring, Red Hot Chili Peppers, Jelly Roll, and Cypress Hill, others flocked to the Harley-Davidson Museum grounds to check out the thousands of visitor motorcycles parked on the grounds, as well as those stationed within the museum itself. The HD Museum is an impressive one, housing an incredible archive of motorcycles and memorabilia dating back to the very beginnings of the company in 1903. Quite early on, it was decided that one motorcycle of each year and model of the production line was to be kept as archival reference, thus there’s no shortage of interesting and obscure metal on display.

21st Century Harley — A Look Back, A Ride Forward

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21st Century Harley — A Look Back, A Ride Forward

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21st Century Harley — A Look Back, A Ride Forward

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21st Century Harley — A Look Back, A Ride Forward

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Interestingly, Harley also dedicates a reasonable amount of space in the museum to the history of motorcycle clubs. Most recently, this archive focused around early women’s riding clubs; it specifically looks at their growth and cultural significance going back decades and decades. Many of these clubs, including the famed Motor Maids — who signed its first charter with 51 members in 1940 — are alive and well today. That same night, at the Veteran’s Park festival venue, I crossed paths with a half dozen members of the Motor Maids — all of whom had ridden into town from neighbouring states. Each was eager to chat, swap stories, and enjoy what was turning into a rowdy night of riders letting loose (responsibly, for the most part).

It’s hard not to see Harley-Davidson’s “old guard” of loyalists in the crowds of Homecoming, but despite that, there’s a statement that was echoed throughout our adventures that couldn’t be faulted. “Harley riders are some of the nicest people you’ll ever meet.”

Sure, you can find rude, unkind, unlikeable folks in any group if you dig deep enough, but like most motorcycle subsets, the folks that embrace the all-American brand proved to be far more welcoming that the gruff, leather-clad exterior would leave some to expect. The brand has been slowly and consistently making headway, expanding its reach into new markets in recent years; it has managed to do so without losing that heart, that enthusiasm, and that passion for all things motorcycles. It’s all a bit like a family; dysfunctional perhaps, unorthodox (likely), but the sense of community and general care for one another is there if you look for it. Just don’t let the loud noise scare you off.