USA: Bourbon, Baseball Bats & The Hot Brown

My husband Jerry and his longtime friend Joe have been talking about visiting the Kentucky Bourbon Trail for years. Thirty years of friendship, countless bourbon pours, and finally the trip was happening. Joe’s wife Cheryl and I signed on as the support crew: there to enjoy the adventure, keep the boys on schedule, and make sure no one forgot to eat.

We went in early October, one of the prettiest months in Kentucky. The trees were just starting to turn, the hills rolled on forever, and every horse farm looked like it had stepped out of a movie. We kept the trip simple: no more than two tours, lots of tastings at the places the guys already knew, plenty of local food and possible sports bars.

Three Days on Kentucky’s Bourbon Trail
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Day 1: Louisville Warm-Up
We flew into Louisville around 5 p.m., picked up the rental car, and drove fifteen minutes to our hotel downtown, the Hilton Garden Inn. We purposely stayed within easy walking distance of The Brown Hotel, the famous Hot Brown, and the exact way we wanted to start this trip.
Even walking into The Brown feels like stepping back in time. The Lobby Bar & Grill has dark wood, tall ceilings, and that soft evening hum of people unwinding over cocktails. We ordered wine, bourbon drinks for the guys, a salad, and the Hot Brown for Jerry and me to share.
The Hot Brown was invented here in the 1920s by chef Fred Schmidt as a late-night snack for glamorous dance-hall guests. It’s thick Texas toast topped with roasted turkey, smothered in creamy Mornay sauce, dotted with tomatoes, finished with crispy bacon, and baked until bubbling and golden. It’s so iconic that Louisville even celebrates Hot Brown Week, complete with cook-offs.
Go ahead and make reservations if you want a table; walk-ins can usually find a seat in the bar area.
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Day 2: Downtown Louisville: Bourbon 101 & Baseball Bats
We started the morning with brunch at Wild Eggs, a local breakfast favorite. Strong coffee, friendly staff, and a good base before a day of bourbon.
Walking through downtown, we met Derrick, a member of the Downtown Ambassador Program—and our first highlight of our morning. He spotted us from half a block away, practically sang and danced to meet us. We looked at each other as he approached and thought uh-oh, who is this guy? Well, his job is to greet us, explain the city layout, and, oh, tell us about his son—who happens to play football for the University of Louisville—all in one breath. We promised we’d watch the game later. He was fun!

Our first bourbon stop was the Evan Williams Bourbon Experience on Whiskey Row. It’s more of an immersive visitor center than a working distillery, but it’s the perfect “Bourbon 101.” Historic scenes, simulated production, and guided tastings set the stage for starting the “morning”.
Afterward, we walked ten minutes to the Louisville Slugger Museum & Factory, easy to spot thanks to the giant bat leaning against the building. The factory tour was surprisingly fascinating, watching how bats are turned, sanded, and branded for major players. At the end, everyone gets a mini Louisville Slugger. Family friendly and the do not serve bourbon. But they do next door to the Museum.
From there we wandered back toward Whiskey Row and dipped into Old Forester Distilling Co., of the Brown-Forman family. In 1870, founder George Garvin Brown became the first to sell bourbon in sealed glass bottles, a life-saving improvement over the questionable barrel blends many people were getting sick from. We didn’t take a tour here, but George’s Bar on the first floor made a fine cocktail stop.
Our last Louisville distillery of the day was Angel’s Envy. Their tour was my favorite. Warm mash samples straight from the vats (weird), a peek at the bottling line (full of very cheerful employees), and a guided tasting with a chocolate pairing. This one is worth booking ahead.
We ended the night at Troll Pub Under the Bridge, a historic underground bar with brick walls, comfort food, and an 8-foot-tall troll greeting you at the door. A loud, quirky, easy way to wind down. Sit in the dining room and watch the game to save your eardrums and have conversations.

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Day 3: Bardstown — Small Town, Big Bourbon
We drove forty-five minutes to Bardstown, often called the “Bourbon Capital of the World.” Breakfast was at Mammy’s Kitchen & Bar, a friendly spot serving Southern classics and—because this is Kentucky—coffee spiked with bourbon if you want it. And I did! This place was exactly what I had pictured: wood walls, checkered tablecloths, family including kids waiting tables.
Being in downtown Louisville was good as a starting place, but getting out on the open road was what we came for! Our first Bardstown stop was the Heaven Hill Bourbon Experience, just minutes away. Heaven Hill is the largest family-owned distillery in America, and it comes with a wild history. In 1996, a massive fire destroyed seven rickhouses and 90,000 barrels, sending burning bourbon running like a river. Imagine seeing that! They rebuilt and grew even bigger.
The place was packed because there was a Ragnar race and Heaven Hill was a stopping point for the runners. We skipped the tour and headed straight to the upstairs bar. The way it works is you stand in line, order your drinks and find a table. Pro tip: sit at the bar itself—no line, great service, and great drinks.

Five minutes away is Willett Distillery, set on a former family farm. The grounds feel like a charming estate, and The Bar at Willett is a gem. Flights for the guys, a seasonal Halloween-inspired drink for me, ice cream for Cheryl, our designated driver—it was perfect. I really liked this place especially for the grounds and the main house.
Our final Bardstown stop was Bardstown Bourbon Company, a modern contrast to all of our other historic spots. Sleek design, glass walls, and a focus on blending and producing custom mash bills for other brands. A good final tasting before we headed back to Louisville for the night. Some people may have slept on the way back to town . . . just sayin’.
Dinner was at Swizzle, the revolving rooftop restaurant on the 25th floor of the Galt House Hotel on the river in Louisville. The view is outstanding. We knew we wanted to have the bartender to talk to and bounce ideas off of. So, we sat at the bar to avoid the slow spin, enjoyed drinks, steaks, and the nighttime city views.
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Day 4: Buffalo Trace, Woodford Reserve & Four Roses
Our third day involved more driving but very doable. Breakfast was at First Watch in Frankfort just under an hour away. Then we headed to Buffalo Trace Distillery, an easy ten minute drive. It’s one of the oldest continuously operating distilleries in the country. Even without reservations, you can join the walk-up tasting lines. We got to try three bourbons and a rye. It’s a cool setup. But since we had no reservations for a tour, we stood in line after line to enter, to taste and to shop. And, did I mention it was somewhere around 80 degrees out? Way too hot. Glad we went and glad we left.
From here, the drive to Woodford Reserve Distillery in Versailles, KY is one of the prettiest stretches in Kentucky—horse farms, stone fences, and rolling fields. Woodford feels like a luxury golf clubhouse, with a beautiful outdoor seating area. We enjoyed flights and cocktails before driving on to Four Roses Distillery. Remember! We had a designated driver!

Four Roses looks a bit different with Spanish Mission-style architecture. It’s calm, peaceful, and really a lovely place for a final tasting of the day. By the time we got there, it was really subdued. We sat inside at a high top since the outdoor tables were full.
We wrapped up with happy hour at Bungalow Joe’s, a sports bar chosen partly because Joe likes places with his name on them. We watched the University of Louisville game (for Derrick’s son!), had a couple of beers and nachos then headed back downtown for one last toast and dinner at The Seelbach Hotel. More old school for me! I love the historic hotels and if I don’t stay there, I at least always make our travel team go there for food and drinks! We hung out in the Old Seelbach Bar for dinner and drinks. F. Scott Fitzgerald once hung out here way back in the day.
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Day 5: A Final Stop at Maker’s Mark
On our way out of Kentucky, Jerry and I stopped at Maker’s Mark in Loretto. This place is gorgeous. I love, love, loved it! Think low stone buildings, bridges over creeks, Chihuly glass installations glowing across the grounds and what feels like an art gallery as you step up to the reception desk. The Samuels family story is legendary: Bill Samuels Sr. literally burned the family’s old recipe to start fresh, and his wife Margie created the iconic bottle design, label and red wax seal. You walk into the Visitor’s Center and it’s an art gallery!
We arrived right when they opened, ordered Ave Marias (a Bloody Mary variation with nasturtium-infused Maker’s Mark Cask Strength), and sat outside overlooking the property. It was the perfect quiet ending to a lively, bourbon-filled adventure.
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Final Thoughts
You don’t have to be a bourbon expert to enjoy Kentucky’s Bourbon Trail! Between the history, the architecture, the small towns, the river views, and the friendly people, there’s something for everyone. Go with a simple plan, leave space for surprises, and don’t skip the Hot Brown.
And if you run into Derrick downtown… tell him we kept our promise and watched the game.

Louisville, Kentucky-Bourbon & Beyond