Louisville, Kentucky, a City of Tradition and Transformation | Wine Enthusiast
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Louisville, Kentucky, a City of Tradition and Transformation

As my car meandered down a winding tree-lined road in search of the entrance to Jonabell Farm, a seemingly perfect song popped on the radio: Luke Bryan’s “Rain is a Good Thing.” Rain makes corn Corn makes whiskey I couldn’t help but laugh aloud—in the backseat, a couple of bottles of Kentucky’s native corn-based Bourbon sloshed along in rhythm, a happy accompaniment with every hitch in the road.

Here in Kentucky, Bourbon and horses are forever linked—just look at the horse-and-jockey stoppers employed by Blanton’s Bourbon, or the Mint Juleps that flow freely at the annual Kentucky Derby. Both are part of the fabric here.

Thoroughbreds in Kentucky
Photo by Monica Stevenson

Louisville is the logical launch point to get a taste of it all.

In recent years, the city has swelled with new restaurants, many of which emphasize farm-to-table or regional takes on Southern-inspired dishes. Meanwhile, urban distilleries that make Bourbon and other spirits, as well as bars that serve them, have also multiplied.

A short drive provides additional opportunity to embark on distillery adventures in a more bucolic setting, full of sprawling thoroughbred farms.

As you hit the road between town and country, don’t worry if a few raindrops splash the windshield. Like the song says, you know what that makes.

Maker's Mark Distillery
Maker’s Mark Distillery / Photo by Monica Stevenson


Start with a night in Louisville, which has no shortage of great bars at which to drink. But first, of course, visit some distilleries.

Tour one or two of Louisville’s urban distilleries, which are growing in number. A visit to Angel’s Envy Distillery or Kentucky Peerless Distilling Co. will give you a glimpse of how the local whiskey is made and usually concludes with a nip of Bourbon. Avoid tourist trap “Bourbon Experiences”—they’re little more than glorified gift shops.

Heaven Hill Distillery
Heaven Hill Distillery / Photo by Monica Stevenson

After dark, the bars beckon. Located downtown, Meta is a craft-cocktail draw with offbeat drinks and zero pretense. In Louisville’s Germantown neighborhood, owner Larry Rice has described The Pearl of Germantown as “the basement bar I wish I could invite strangers to.” It has a relaxed vibe and a wheel of drinks for indecisive souls in need of cocktail intervention. Rice also owns The Silver Dollar in Clifton, noted for its extensive Bourbon selection and honky-tonk feel. A couple of doors down, inside the century-old Hilltop Theater building, Red Herring sports a list of 100 cocktail classics, as well as plenty of “house concoctions.”

Angel's Envy Distillery
Angel’s Envy Distillery / Photo by Monica Stevenson

The next day, rent a car or take the Mint Julep tour bus to visit more traditional distilleries farther afield. At these places, you can tour the grounds and inhale the caramel-scented perfume of a rickhouse, where the barrels age. You won’t be able to hit them all in a single day, but some worth a visit include Heaven Hill Distillery’s Bourbon Heritage Center (Bardstown), Woodford Reserve Distillery (Versailles), Maker’s Mark Distillery (Loretto) and Wild Turkey (Lawrenceburg). There’s also up-and-comer Jeptha Creed Distillery (Shelbyville), which hosts concerts and other events.

Keep an eye out for one of the four distillery cats, each named for a grain used to make whiskey.

Jack Fry's
Jack Fry’s / Photo by Monica Stevenson


Proof on Main, within the 21c Museum Hotel, is a favorite for its Southern style and emphasis on dishes made with local ingredients, like the bison burger with jezebel sauce, an apricot-apple-jelly base with horseradish, pepper and other spices. It doesn’t hurt that the eatery boasts more than 120 Bourbons and an intriguing wine list.

Jack Fry’s, established in 1933 as a haven for bootleggers and bookies, offers a glimpse of thorough­bred history. It’s an iconic spot to enjoy an Old Fashioned and take in a collection of assorted sports memorabilia and vintage photographs.

Milkwood / Photo by Monica Stevenson

Celebrity Chef Edward Lee has multiple restaurants in Louisville. Perhaps his best known is the genteel 610 Magnolia, which offers a Brooklyn meets Bluegrass six- or four-course tasting menu. Wine lovers won’t be disappointed here, though Lee also has a standalone Wine Studio across the street. Lee’s MilkWood creatively combines dishes from Asian countries with Southern flavors, like ramen noodles with barbecue tofu and beet-pickled eggs, paired with creative Bourbon cocktails. His latest spot, Whiskey Dry, opened in February, featuring over-the-top burgers and more than 200 global whiskey offerings. The beverage program is overseen by Stacie Stewart, a Wine Enthusiast 40 Under 40 alum.

A short ride across the Ohio River—or a leisurely, scenic stroll across the pedestrian Big Four Bridge—lands you in Jeffersonville, Indiana. Portage House offers expansive views of Louisville and homey fare like Indiana chicken thighs with rice grits, or a juicy fried pork-chop sandwich served with housemade pickles.

Nyquist, retired thoroughbred and winner of the 2016 Kentucky Derby
Nyquist, a retired thoroughbred and winner of the 2016 Kentucky Derby / Photo by Monica Stevenson


Churchill Downs, home to the famed Kentucky Derby since 1875, offers year-round tours through the Kentucky Derby Museum. The Barn and Backside tour starts with a 360° video viewed in swivel chairs. That’s followed by a van ride around the grounds to watch the horses gallop on the racetrack, and it concludes with a visit to the museum. Back at the gift shop, splurge on a ridiculously broad-brimmed chapeau, a must for Derby Day.

Serious about horses? Drive out to the rolling fields of Lexington, where Darley’s Jonabell Farm offers a closer look at the thoroughbred experience. Tour the grounds and sheds, and take photos with some of the farm’s prize-winning racehorses, who are kept and bred here.

The Bourbon & Beyond music festival returns in September. This year’s line-up includes John Mayer, Lenny Kravitz, Sting, Robert Plant, Sheryl Crow and more. Bourbon is also a draw, from master distillers who pour previews of their latest bottlings to tasty Mint Julep experiences, Bourbon workshops and The Big Bourbon Bar, which features exceptional, rare and vintage Bourbons served up in style.

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