Are you heading home or flying out?” the lady with kind eyes sitting next to me asks. “I’m going to Lou-ie-ville!” I answer, not realizing that wasn’t exactly her question. “No, you’re not,” she replies, and I fear I’m on the wrong plane. “You’re going to Looavuull,” she drawls. That was the first true thing I learned about Louisville, Kentucky — how to pronounce it.

It’s late when we arrive at the 21c Museum Hotel in downtown Louisville. I’m groggy from the journey but certain this is the most unusual hotel lobby I’ve ever been in. Behind the front desk, a series of child-like sculptures are staring me down. To my right, a 25-foot silver installation made out of household objects droops from the illuminated ceiling and twists its way down to the lower level like a billowing tornado. The clerk tells me the hotel is also a 24-hour contemporary art museum, free to the public. I’ve never slept in a museum before.

The next morning, I go for a leisurely stroll outside the hotel along Main Street’s red-brick sidewalk. I’m heading towards a specific one-block stretch known as Whiskey Row. After all, whisky is why I’m here — bourbon is in Kentucky’s blood. For those new to the spirit, like me, the most important thing to remember is that all bourbon is whisky, but not all whisky is bourbon (and Canadians spell it ‘whisky,’ sorry).

In the mid-1800s, the small but mighty Whiskey Row was overflowing with the amber liquid. Beyond the buildings’ cast-iron facades — many of which have been preserved and still stand today — whisky barrels from nearby Kentucky distilleries were stored and sold. Hundreds of barrels left the state via steamboat to places like New Orleans, where bourbon allegedly got its name. People started asking for the whisky from charred-oak barrels sold on New Orleans’ Bourbon Street — that whisky was made in Kentucky. Business was booming until 1920, when Prohibition crashed the party. But, while many operations closed, the production and consumption of bourbon didn’t stop: It just went underground.

West of Whiskey Row, I find the front doors of the Evan Williams Bourbon Experience. I’m right on time for our tour, but late according to southern hospitality standards — everyone is already there, patiently waiting with unbothered smiles near the back stairs that we trickle down.

When we reach a lonely door in the basement, the lady who led us here swings it open to reveal another door. The tallest man in our group taps on the door. A tiny slit slides open from the other side. “I’m looking for a good old fashioned, and I brought some friends,” the tall man says into the opening. The group giggles. “That’s not it!” someone yells. He clears his throat and tries again, “I’m looking for the ideal bartender…” The door opens slowly to reveal renowned Louisville bartender Tom Bullock, the first African American person to publish a cocktail book.

I should note that Tom Bullock died in 1964. But right now, he is very much alive because it’s 1933, and we’re at a hush-hush speakeasy for some Kentucky bourbon, old fashioned cocktails à la Tom (he uses a lemon peel instead of an orange), and stories told around a worn wooden bar. This ‘Ideal Bartender Experience’ is part of Louisville’s ‘Unfiltered Truth Collection,’ which highlights the often untold stories of African American trailblazers such as Bullock, who perfected cocktails, including the old fashioned and mint julep (the official drink of the world-famous Kentucky Derby).

Louisville, Kentucky Bourbon | The Ideal Bartender Experience at Evan Williams Bourbon

The Ideal Bartender Experience at Evan Williams Bourbon

It’s 1 p.m., a little early for bourbon, but I figure it’s my 29th birthday, so what the hell. Part history lesson, part tasting experience, we learn some of the laws that make bourbon, bourbon: It must be made in America from a mash bill of at least 51 per cent corn; aged in new, charred-oak containers; and can’t be more than 62.5 per cent ABV when it goes into the container (usually a barrel) for aging. All these nuances — alcohol content, char level, and where the corn and other grains grow (among many other factors) — give each bourbon its distinct flavour profile.

It’s a little early for bourbon, but I figure it’s my 29th birthday, so what the hell

We raise our glasses, the sound of clinking ice cubes echoing in the subterranean space, and toast to “those who enjoy snug club rooms, may they learn the art of preparing for themselves what is good.” And with that, it’s time for a fried-chicken sandwich from Royals Hot Chicken and a good nap.

That evening, we have a reso at Proof on Main, the equally creative and quirky restaurant inside the 21c Museum Hotel. Here, staff bounce around the dining room wearing their own vibrant clothes, which complement the bright flowery wallpaper and striking framed prints and photographs. Our server has lavender-dyed hair and asks us what we thought Louisville was like before we visited. “Not this,” I gesture to the restaurant.

The menu showcases the best of Louisville’s surroundings, from bison raised on a sustainable farm 30-minutes away to seasonal ingredients, and, yes, bourbon makes an appearance. “It’s one of those things where you want to make sure it’s there, but you don’t want to beat the hell out of it,” says executive chef Jeff Dailey. “You want bourbon to be present but not so flashing in front of everyone’s face that they get sick of it.”

Dailey doesn’t pour bourbon in the pan and call it a day. “That’s such a cop-out. Where’s the creativity?” he stresses. Instead, the kitchen incorporates bourbon subtly by fermenting cabbage in a former bourbon barrel for southern-style kimchi, or using leftover grains to make bread.

“We’ll take the staves (slightly curved wooden strips) out of the barrel and use those for smoking. There’s a great company down here called Bourbon Barrel Foods. They make bourbon-barrel soy sauce, Worcestershire, smoked salts and spices that allow us to incorporate that history and nuance without us just pouring bourbon into things,” says Dailey. Bourbon is meant to be poured into a glass — like the several we had at the sultry Hell or High Water cocktail lounge after dinner — not onto your plate.

At 9 the next morning, puffy-eyed and feeling closer to 30 than ever, we hit the (breakfast) Bourbon Trail. First stop, the iconic Maker’s Mark distillery in Loretto, a one-hour drive outside of Louisville.

Sitting on 1,000 acres, ‘the campus,’ as it’s referred to, is more like a small, 1950s storybook town with rolling green hills, flowing streams, and quaint houses brushed in black paint and pricked with bright red shutters. “It’s like Disneyland for adults,” jokes Amanda Humphrey, education and experience manager, who takes us through the distillery’s many fascinating components.

It’s like Disneyland for adults

We can smell the pungent fermentation room before we set eyes on its enormous wooden tanks bubbling with mash — picture a wooden barrel of oatmeal for giants. “We keep true to the same recipe that we’ve been using since 1954,” explains Humphrey. The addition of red winter wheat gives Maker’s Mark Bourbon that touch of sweetness and a gentler sip that doesn’t melt your face.

Maker’s Mark is known for honouring the past. They are one of the only distilleries that still rotates barrels by hand. A 1935 printing press makes the labels. And each bottle is hand-dipped in molten red wax (distillery visitors can give it a go). These processes aren’t efficient — and that’s the point. “I love that we protect the founder’s vision and the taste profile of Maker’s. We don’t modernize if it means the taste is going to change,” says Humphrey.

For Maker’s Mark, protecting these traditions is more important than being the fastest or the biggest producer. Everything about them feels intentional. As much as Maker’s Mark is rooted in the past, they are passionate about safeguarding the future through sustainable practices like turning old Maker’s Mark bottles into sand for hiking trails and joining the B Corp global community.

If there’s a distillery with its eyes set on the future, it’s Bardstown Bourbon Co., where we head to next. Upon first glance, the modern glass-walled distillery seems like the opposite of Maker’s Mark. “We honour tradition, but we’re always pushing the boundaries of innovation,” says Logan Dunbar, brand education lead.

He shows us the ins and outs of the distillery, from its state-of-the-art rickhouses (where bourbon is aged) to the stainless steel fermentation tanks surrounded by screens. “We operate on a smart system called ‘Ignition.’ We’re the first distillery to use it,” he explains. “We measure and track 500 variations of distillation, not only for our products but for over 30 customers.”

At only eight years old, Bardstown Bourbon Co. has established itself as a leader, as well as an incubator for both recognizable and newer brands — and a few celebrities. Perhaps the coolest room of all is their private vintage library of rare bourbons, showcasing present-day gems alongside pre-Prohibition bottles dating back to 1892 — all available to taste by the ounce.

“Without that foundation set from our amazing predecessors, we would not be as successful as we are today,” says Dunbar. “You can’t know where you’re going if you don’t know where you’ve been.” Standing among bourbon legends, I’m inclined to agree. But I think there’s something to be said for not knowing where you’re going and letting yourself be absolutely, wonderfully surprised.