Three Days in Louisville: A Return to the Big City of Yesterday
By Jenna McMaster
When I was a child growing up in rural Kentucky, Louisville was the “big city,” a place full of bright lights and people in a hurry, where my father would take me when he had to sell the bee hives he’d built in our barn. I remember the way the city seemed to hum as we drove in, its skyline a jagged teeth smile against the sky.
We’d park near the hardware store, a dusty old place that smelled of wood shavings and sawdust, and I’d follow him inside, pretending to look at the tools while he talked business. It was his world, but it was a world that fascinated me, with its noises and smells so different from the quiet of our farm. Now, decades later, I’ve come back to Louisville on my own terms, ready to see the city not just through the eyes of a girl from the country, but as someone who has traveled the world and still believes that small things can mean a lot.
Louisville has grown up since those days, and so have I. The city has its own rhythm, a mix of Southern hospitality and a restless spirit that I’ve come to appreciate more and more as I’ve gotten older. Over the next three days, I’ll be revisiting old haunts and discovering new ones, soaking up as much of the city as I can, one bourbon sip at a time.
Day One: Arriving and Exploring Downtown
I arrived at Louisville's 21c Museum Hotel, an art hotel that could easily double as a modern art gallery. When you walk in, you're greeted not by a bellhop but by a giant, bright red penguin. It’s an odd choice for a lobby mascot, but I like the idea that this place doesn’t take itself too seriously. The penguins are a theme here—scattered throughout the hotel, standing guard over hallways, elevators, and occasionally a lost guest. My room is minimalist, with sleek furniture and art that’s meant to make you think—or at least make you question your own taste. I threw my bags on the bed and went down to the lobby, where I was handed a map to the hotel's contemporary art exhibits. I could have spent hours wandering the halls, but the city outside was calling.
First stop: the old hardware store. It’s still there, somehow, a relic of another era amidst all the new construction. I went inside and found myself talking to the man behind the counter, who looked at me like I was crazy when I told him I used to come here with my father to sell bee hives. “Haven’t seen any bee hives in years,” he said. “But we still got the sawdust.” I laughed and bought a small hammer, just for old time's sake. Outside, I walked down Main Street, past the Louisville Slugger Museum & Factory, where they still make bats for the big leagues. I could see the giant bat leaning against the building from blocks away, a testament to a city that knows how to celebrate its past without being stuck in it.
Day Two: Sipping Bourbon and Remembering Roots
I started my second day with a visit to the Kentucky Bourbon Trail, because when in Louisville, you drink bourbon. Or at least pretend to know what you’re doing when you drink it. I booked a tour with Old Forester, the oldest distillery in Louisville and a place that still takes its craft seriously. The smell of fermenting mash hit me as soon as I walked in, a sour, earthy scent that brought back memories of my father making moonshine in the barn. Our guide led us through the distillery, explaining the intricacies of bourbon-making as we went. I nodded along, though I was more interested in the barrels, lined up like soldiers ready for duty. At the end of the tour, we had a tasting, and I learned that I still don’t know how to properly drink bourbon. But I also learned that it doesn’t really matter, as long as you enjoy it.
From there, I walked to The Brown Hotel for lunch. It’s one of those grand old places that has seen better days but still retains a certain charm. I ordered the Hot Brown, an open-faced turkey sandwich smothered in Mornay sauce and topped with bacon, which was invented here during the Roaring Twenties. It's decadent, a dish that could only be invented in a city that isn’t afraid to indulge. I ate slowly, savoring the mix of flavors and the sense of history that came with each bite. Outside, the city was waking up from its afternoon lull, ready for another night.
Day Three: The Park and a Night on the Town
I spent my final day at the Louisville Mega Cavern, a massive former limestone mine turned adventure park that runs under the city. I had signed up for the zip line tour, thinking it would be a fun way to see a different side of Louisville. What I didn’t realize was just how far underground we’d be going. Our guide, a cheerful young woman who seemed entirely too enthusiastic for someone about to fling herself off a platform into the abyss, gave us a quick safety briefing and then sent us on our way. I screamed like a banshee the first time I went, but by the third line, I was starting to enjoy myself. There’s something about being underground that makes you feel like a kid again, exploring places you’re not supposed to be.
That night, I decided to treat myself to a nice dinner at Proof on Main, the restaurant inside the 21c Museum Hotel. The menu is a mix of Southern staples and modern twists, and I ordered the bison burger, which came with a side of truffle fries that I’m pretty sure could make anyone a believer. The place was packed, the kind of crowd that’s here to see and be seen, but I was more interested in people-watching. There’s something about dining alone in a nice restaurant that makes you feel both invisible and all-seeing, like you’re a part of the scene but also just outside it.
After dinner, I headed to the Highlands neighborhood, a lively part of town known for its bars and nightlife. I ended up at The Silver Dollar, a honky-tonk housed in an old fire station. It’s the kind of place where you can drink good whiskey and dance to live music without feeling self-conscious. I found a seat at the bar and ordered a bourbon, neat this time, and watched the crowd. There were college kids trying too hard and couples who’d been coming here for decades, and I felt a strange sense of belonging. It wasn’t the same city I remembered from childhood, but it was a city I could see myself coming back to, again and again.
Epilogue: Leaving but Not Saying Goodbye
As I packed up to leave the next morning, I thought about how much had changed since those early days coming into Louisville with my father. The city has grown, sure, but it’s also held on to its roots, much like the old hardware store with its dusty shelves and lingering smell of sawdust. I’m not the same girl who used to tag along behind my father, but I’m also not so different. I still love the smell of wood and the taste of bourbon, and I still find something magical about a place that knows how to keep one foot in the past while stepping boldly into the future. As I drove out of town, I looked back at the skyline one last time, that familiar jagged smile against the sky, and I knew I’d be back.
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