Riding Through Memory Lane: A Three-Day Journey in Milwaukee

By Jennifer Sullivan

The rumble of the engine beneath me was like a heartbeat—steady, fierce, alive. I swung off my bike in front of the Iron Horse Hotel, leather jacket clinging to my shoulders, my well-worn jeans tucked into scuffed riding boots.

I caught a glimpse of myself in the chrome of a parked Harley—a flash of black leather and nostalgia. Not for my youth, exactly, but for the man in the faded photo I’d kept in a box for years. Dad, sitting on a Harley, one of the only pictures I had of him. I’m still not sure it was even his bike. It didn’t matter. It was his stance—the casual grip on the handlebars, the smile that looked like freedom and recklessness rolled into one.

Funny thing is, it was my ex-boyfriend, not my father, who took me for my first ride. I was sixteen, and it was love at first throttle—the speed, the noise, the way the world blurred as you tore through it. That boyfriend is long gone, but the love of motorcycles? That stuck. So, here I was, decades later, in Milwaukee—the birthplace of Harley-Davidson—not to chase ghosts, but to feel the weight of history rumbling beneath my feet.

A Room with a Roar

The Iron Horse Hotel doesn’t pretend to be something it’s not. It’s gritty, industrial, unapologetically tied to its roots (that’s the bar above). This place once housed saddles and bridles, back when horsepower meant something you fed and groomed. Now, it caters to a different kind of rider—the kind who doesn’t mind paying extra for a suite with exposed brick walls and leather headboards. My room had a view of the river, though I barely noticed; I was too caught up in the details—saddle blankets on the bed, old factory beams framing the windows, the faint scent of wood polish and leather. It made you feel like part of something bigger, like you’d stumbled into a club you didn’t even know you wanted to join.

I tossed my bags on the bed and grabbed my jacket. My first stop? The Harley-Davidson Museum. Because if you’re going to pay homage to the past, you might as well do it surrounded by chrome, steel, and history that smells like oil and freedom.

Lunch with a Side of Grit

After losing myself in the roar of history at the museum, I needed fuel—both for me and my bike. Sobelman’s Pub & Grill was the obvious choice. The locals swear by the place, and I’d heard factory workers frequented it. Perfect.

Sobelman’s was everything I wanted it to be—loud, bustling, and unapologetically divey. The burger I ordered? Let’s just say it was a behemoth—two thick patties, cheese that oozed from the sides, and bacon crisp enough to snap with a glance. It came with a Bloody Mary that was less a drink and more a five-course meal, complete with skewers of cheese, sausage, and shrimp piled on top like a dare. The people here had grease-stained hands and laughed the way you do when you’ve put in a full day’s work. They made me feel like I belonged.

As I debated whether to finish the burger, I thought of Dad again—not in a sad way. More like a quiet acknowledgment that I’d found my way to something that had been his, but was now mine. I wasn’t chasing his ghost anymore. I was carving my own path, one bite at a time.

Harley Factory: Building Freedom

The next morning, I zipped up my leather jacket and headed out for a tour of the Harley-Davidson factory. There’s something humbling about seeing a machine built piece by piece, knowing that it will one day carry someone across miles of asphalt. The factory floor was a mix of precision and chaos—workers in overalls assembling each bike with practiced ease. Watching the frames come together, knowing the bikes would soon be roaring down highways, I felt a strange sense of pride. Not just for the workers, but for myself. Harley-Davidson wasn’t just part of my past; it was part of my story.

That night, I swapped my riding boots for something more subtle—ankle boots with just enough heel to feel a bit dangerous—and headed to Bryant’s Cocktail Lounge. The low lighting, velvet booths, and vintage vibe made it feel like a speakeasy stuck in time. I ordered a Brandy Old Fashioned (it’s Wisconsin law, after all), and sipped as I watched the bartender mix drinks with an almost reverential precision. Bryant’s isn’t the place for a wild night out; it’s a place for reflection, for soaking in the moment, for letting the city breathe around you.

Milwaukee at night has an energy that’s hard to describe. It’s not loud like New York, or in-your-face like Chicago. It hums quietly, letting you take it all in without rushing you.

A Ride to Remember

On my final day, I headed to a Harley-Davidson dealership just outside the city. I wasn’t looking for a new bike—at least, that’s what I told myself—but standing in a showroom filled with shiny new Harleys is enough to make anyone reconsider. I ran my hands over the chrome, imagined the open road stretching out in front of me. There’s a thrill in the possibility, in knowing that at any moment, you could ride away from it all.

As I mounted my own bike later that afternoon, the weight of the city—and everything it had shown me—settled over my shoulders like my favorite leather jacket. Milwaukee hadn’t given me all the answers. But it had given me something better: the freedom to ask new questions.

As I roared out of the city, the wind in my face and the hum of the engine beneath me, I couldn’t help but smile. This trip wasn’t about finding the man I’d lost. It was about finding myself—and realizing that was more than enough.

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