Whiskey Row Walking Tour: Louisville Native Drew Shryock Shares Bourbon, History, and Pride

September 29, 2026/in Culture, Hospitality/by Mikhayla Hughes-Shaw

Whiskey Row Walking Tour founder and owner Drew Shryock is a lifelong Louisvillian, a proud gay man, and a bourbon lover. He also considers himself a community builder, especially after spending 22 years working for Louisville’s Economic Development Department. Now retired, Shryock knows his city inside and out.

Shryock leads tourists through the city’s historic Main Street, celebrating the culture, the people, and the places that make Louisville unlike anywhere else in the country — or the Commonwealth. He’ll also tell you, with a grin, that Kentucky makes about 95 percent of the world’s bourbon.

“There are a few other states that make the other 5%, but we call that artificial bourbon,” he says, “because we make the real thing here in Kentucky.”
Culturally and fiscally, bourbon is a staple for the Bluegrass state, as Kentucky Bourbon remains a key and substantial contributor to the state’s economy, with a $10.6 billion industry supporting nearly 24,000 jobs. Personally, for Shryock, his love of the craft started from a young age. He fondly remembers Sunday family dinners with his mother and grandmother, who sipped highball cocktails while preparing the meal.

“One time I asked my mom, ‘Can I have a sip of that?’ She said, ‘Yes, you can have a little sip.’ And that was my first exposure to bourbon. And I fell in love with it. I hate to say that, but I did,” he tells Queer Kentucky.

He believes he came by his now-matured love of the spirit naturally.

“If you’re born in Kentucky, bourbon’s basically in your blood. It really is,” he says.

How the Whiskey Row Walking Tour Started

After leaving the workforce, Shryock took time off to recover from his 9-5 days. After about 6 months, he started helping out as a driver for visitors on the Kentucky Bourbon Trail. He enjoyed meeting folks from all over and hearing their stories, but he also found that distillery visits weren’t always a guarantee.

“People would say things like, ‘We tried to get into such-and-such distillery downtown, but it was full, and we couldn’t get in. We tried to go to this distillery, and it was full.’ So, I kept thinking: there’s got to be an [easier] way I can take people into these distilleries,” he says.

So, he tried something new.

“I met with several distilleries individually. I basically cold-called them. I explained who I was, my history with bourbon, my history with the city…and asked them if they would be interested in being part of my walking tour downtown. And that’s when I came up with the concept of the Whiskey Row Walking Tour in downtown Louisville,” Shryock says.

As his knowledge grew, so did his love of the craft.

“Going to the distilleries, meeting the people who work at the distilleries, and getting to know some of the master distillers at the same time…sparked my passion,” says Shryock.

What Happens on the Tour

The Whiskey Row Walking Tour has now been operating for more than four years. Intimate groups of up to twelve people gather at the Kentucky Bourbon Trail gift shop inside the Frazier Kentucky History Museum to start. From there, he leads the group on a two-hour stroll down Main Street – better known as Whiskey Row. Guests sip their way through some of the city’s most iconic pours, including tastings at Bardstown Bourbon Company and the Evan Williams Bourbon Experience, the first distillery back on Whiskey Row since before Prohibition.

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He acts as a conductor of stops and stories along a theoretical railroad (or, just about six blocks or so) of distillery stops, allowing each business’s guide to take center stage during tours. He fills the in-between time with jokes, fun facts, and a few tricks.

Shryock also turns Main Street itself into the lesson. He tells guests about how Louisville is home to the country’s second-largest collection of cast-iron storefronts, and walks guests past the sites of former distilleries.

“I wear a name tag that’s a magnet, so I’ll take the magnet off my name tag, walk right up to those cast-iron buildings, and it adheres right to the middle,” he says.

“When I take my magnet off and put it on the cast-iron metal, they just go crazy,” he adds with a laugh.

After a few pours and countless inside stories, the tour ends in the pre-Prohibition heart of Whiskey Row, between Brook, First and Second streets, where names like Old Forester and Pappy Van Winkle’s W.L. Weller & Sons once operated until being shut down in 1920. By the last stop, the group that started out as strangers usually leaves as friends, with a new appreciation for Kentucky’s favorite spirit and the city that made it famous.

“You take a group of complete strangers, and they’re all enjoying each other’s company by the end,” he says. Of course, the bourbon helps, he jokes. “Once we do that first tasting, barriers start melting… And by the time we do the second and third tasting, you would think they were all friends. That’s what I love about it.”

Showing Up as Himself

When meeting folks from all over, Shryock says he may run into guests who don’t always agree with his “lifestyle” or sexual orientation. But that does not stop him from being authentic in how he shows up.

“Not everybody has to accept you. You have to accept yourself first,” he says.

He hopes to encourage folks to confront their biases, simply by spending time with him on a tour.

“I’m very proud of who I am as an individual. And I’m very proud of my sexual orientation,” he tells Queer Kentucky. “The more exposure we have around [other kinds of] people, the more walls get broken down… So they say, ‘This is a good tour. I really liked him. Maybe I need to start reevaluating some things in my life, the way I view people.’”

As for Bourbon & Belonging and its importance, the idea of belonging is what is most important to him. Shryock says it’s reassuring to see more safe spaces being intentionally created for queer folks. In the 80s and 90s, Shryock recalls gay-owned bars acting as safe havens for him and his gay friends.

“That was really the only safe space where we could gather without the fear of being harassed, or some type of physical violence happening to you…We knew there was safety being there, and we all kind of had each other’s back,” he says.

He appreciates how queer people can exist without as much ridicule, but still recognizes there is work to be done.

“Thank goodness it isn’t how it used to be,” Shryock says.

The Whiskey Row Walking Tour runs from Friday to Sunday, October 2nd-4th. You can book your spot here.

Shryock is most excited to expose more folks to his favorite city: “As a native Louisvillian, I’m very proud of our city, and I love to show it off.”

Disclosure: Bourbon & Belonging is produced by Queer Kentucky.