Our Kentucky Bourbon Trail Tour: A Spirited 3-Day Whiskey Itinerary

To understand bourbon culture in Louisville, Kentucky, you must first understand bourbon.

Whiskey is any liquor that has been fermented and distilled from any type of grain. Bourbon is defined by the U.S. government as a type of whiskey that has been created within specific conditions. For example, the bourbon must be fermented from at least 51% corn. Bourbon must be aged in new oak barrels that have been burned inside, leaving a charred surface in contact with the maturing liquor. And, to qualify as bourbon, the whiskey must be made anywhere in the U.S.

However, do not say that last sentence to anyone in Kentucky. 

Kentucky, and only Kentucky, is the undisputed center of bourbon culture in America. Every major bourbon distillery in the U.S. is based in Kentucky, where families of distillers trace their roots back to the 1700s, before Kentucky was even a state. 

Farmers from Ireland and Scotland who settled here already knew how to ferment their unsold crops into whiskey (which was the Irish spelling; the Scots use whisky), but it was the pure, mineral-free water from Kentucky’s underground limestone aquifer, the largest in North America, that led to a particularly tasty drink. 

Steamboats loaded with barrels of precious Kentucky bourbon traveled up and down America’s waterways until Prohibition devastated the industry in the 1920s. Although a small group of distilleries received legal permission to continue production for medicinal purposes (whiskey was used as a painkiller at the time), most of the U.S. distilleries shut down and instead cooked up tubs of impure, un-aged, illegal moonshine. Even after Prohibition ended in 1933, it took decades for U.S. distilleries to repair their reputation.

Now, a century later, as more of distilleries churn into existence, Kentucky’s bourbon is again a standard of quality among connoisseurs. Approximately 100 distilleries now produce bourbon in Kentucky, and the region has grown into a world-class tourist destination. 

Partly driving that popularity, the Kentucky Distillers Association created the Kentucky Bourbon Trail in 1999 to promote visiting distilleries all over the state. There’s no actual path to follow, but there is a map dotted with places to go.  Because distilleries can pay to be included on it, not every location it lists is necessarily worth visiting. 

We can help. With so many picturesque Kentucky estates to drink in—and so many great things to actually drink—here are some great ideas for planning your journey into bourbon country. These make a great start to understanding and enjoying this uniquely American spirit.

Bourbon is in the air in Louisville, sometimes literally as the aroma wafts from distilleries. Bartenders across the city guard arsenals of bottles, from Kentucky’s finest like Jim Beam and Maker’s Mark, to so-called "dusties" from decades ago that can cost $200 per pour. 

Angel’s Envy is a relatively new bourbon brand, created in 2011 by master distiller Lincoln Henderson, who had previously created the upscale Woodford Reserve bourbon. Angel's Envy is a no-nonsense distillery where guides delve into the science of their craft while cracking occasional jokes. It's also one of the few distilleries that's located in the city of Louisville, so it's a good choice for visitors who don't want to drive after sampling bourbon. Angel’s Envy's product has a spicy, tongue-tingling kick, but it also bottles a rye whiskey that is buttery soft and sweet.

After tastings and tours at Angel’s Envy, walk directly across the street to Louisville Slugger Field, home of the Triple A baseball team Louisville Bats, and sit on the patio for some burgers and beers, no game ticket necessary. The Louisville Slugger bat museum and factory is a little over a mile down Main. 

The Evan Williams Bourbon Experience in downtown Louisville features two floors of educational videos and life-sized exhibits about Kentucky’s bourbon history, and the top floor has the On3 bar and tasting room. Those are a fair introduction to the topic, but breeze through all of that, because the best option is the basement bar, where you’ll find the actual “bourbon experiences.” 

On Thursdays and Fridays, “The Ideal Bartender” leads guests through a tasting of different Evan Williams top-shelf bourbons, guided by an actor (above) who plays George Kappeler, one of Kentuckys’ first African American professional bartenders, who is credited for perfecting the recipe for bourbon Old Fashioned. You will then drink one of those perfected Old Fashioneds. It will be the best Old Fashioned of your life. 

On Saturdays and Sundays, Evan Williams offers the Speakeasy Tasting Experience, where you can sample booze recipes from the Prohibition era. This stuff was a bit stronger than what is distilled today, and that first sip will take your breath away. Reservations for all experiences required.

528 W. Main St., Louisville 

In 2013, the mayor of Louisville proclaimed his city “the bourbon capital of the world,” citing the hundreds of millions of dollars that the industry pours into the city through sales and tourism. This boast did not sit well with residents in other parts of Kentucky. Many of them still bristle in defense of a small town called Bardstown, an hour’s drive south of Louisville.

Bardstown has been a hub for Kentucky’s bourbon production since the Revolutionary War years, and some of those original bourbon families are still working here, including the owners of the massive Heaven Hill distillery, which produces multiple brands like Evan Williams and Elijah Craig. Bardstown now has 11 distilleries, including Willett, one of the most well-regarded names in the bourbon industry, and many are open to the public with tours, tasting rooms, and even gift shops that sometimes sell cocktails. 

Bardstown also hosts the Kentucky Bourbon Festival, a three-day extravaganza that happens each September, when guests can partake in unlimited bourbon tastings from distilleries from around the state. Also popular in the Bardstown area: a ride on My Old Kentucky Dinner Train, where you can sip bourbon while you enjoy the glamour of train travel from years gone by. 

Heaven Hill Distillery: 1311 Gilkey Run Rd., Bardstown

Willett Distillery: 1869 Loretto Rd., Bardstown  

My Old Kentucky Dinner Train: 602 N. 3rd St., Bardstown 

Halfway between Bardstown and Louisville, pop in for a visit at James B. Beam. The name is equivalent to Kentucky royalty, and the Beam family of bourbons includes some of the most familiar brands, such as Jim Beam, Basil Hayden, and Knob Creek. Its distillery, located about 20 minutes south of Louisville in Clermont, is a massive property, offering tastings, tours, and a gift shop selling bourbon-themed knick-knacks.

Bourbon tastings can be intense for some folks, as not everybody enjoys drinking undiluted, room-temperature liquor. They are not to be shamed. The Jim Beam distillery, as it is colloquially known, also offers fun cocktail-making classes where participants are guided through the process of making a featured cocktail, with fresh ingredients and top-shelf bourbon. Then after that, they get to drink it.

You can have a meal here, too. Jim Beam is also one of the few distilleries to operate a restaurant—most of them close by dinner time. Here, you'll find burgers, pizza, and other friendly fare, and of course there is a bar with a creative cocktail list, but most of your other restaurant options will be back in Louisville, making it the easiest place to overnight during your explorations. 

568 Happy Hollow Rd., Clermont   

Watch Hill Proper, on the northeast fringe of Louisville, is technically a member’s club, with invitation-only events and specialized whiskey lockers where members can store their own collections. The bar and restaurant, however, is open to the public to share the grandeur of its 1,600 bottles of bourbon and other assorted whiskeys. Any bar can install a ludicrously capacious wall of shelves and fill it with booze, but Watch Hill Proper is staffed by friendly bourbon aficionados who know their inventory intimately and deliver sharp opinions about the merits of each bottle. 

Fred Minnick, who is perhaps the leading whiskey critic in the U.S., has named Watch Hill Proper as his personal favorite watering hole, although it’s also true that he also happens to live down the street. “I can walk there and taste something I do not have in my collection, which is hard to do, like a 1960s Old Forester Bottled in Bond,” Minnick told Frommer’s. “And chef Michael Crouch is a brilliant cook.” And if you don’t know what bottled in bond means, the staff at Watch Hill Proper will gladly explain.

11201 River Beauty Loop, Prospect 

Touring a bourbon distillery is a rite of passage when you’re visiting Kentucky, and no distillery is more picturesque than the estate of Maker’s Mark. Tucked into the hills on a single-lane, pull-over-if-another-car-is-coming country road, the entrance of Maker's Mark welcomes you into the grounds of a distillery that unfold around you, like a Valhalla of Americana. 

Maker's Mark presents a robust schedule of tastings and tours, which include strolls through one of the barrel storage rooms and under a glass ceiling by sculptor Dale Chihuly. Or visitors can just dawdle the day here, wandering paths while sipping cocktails and listening to a bubbling creek beneath gentle tree shade. 

The estate, which was originally founded under a different name in the 1800s, was meticulously preserved by Margie Samuels, an icon of the bourbon industry and partner of master distiller Bill Samuels. Margie directed everything from the updated design of the grounds of the historic distillery to the shape of the Maker’s Mark bottle, and she even invented the recipe for the trademark Maker’s Mark red wax on the cap. Visitors can dip their own bottles in wax, which makes it likely they will never open those souvenirs, so if you dip a bottle, be sure to buy a second bottle to actually drink.

3350 Burks Spring Rd., Loretto   

Remember that comment about Maker’s Mark being the most beautiful distillery in Kentucky? The folks at Buffalo Trace, in Frankfort, and hour's drive east of Louisville, might challenge that. 

Buffalo Trace bourbon entered the market in 1999, but just like Maker’s Mark, its distillery has been operating under various names for centuries. This estate is the Disneyland of distillery country, a grand and glorious campus where bourbon enthusiasts can spend all day exploring old warehouses, distilling machinery, an arboretum, and lovely gardens. History abounds at Buffalo Trace, and the property is listed on the National Register of Historic Places.

The grounds are open to the public, but reservations for tours and tastings require reservations and are highly recommended. There is no bar selling cocktails, but the good news is Buffalo Trace is the only major distillery that offers tours and tastings for free, so of course it’s a popular place for tourists. It is also remarkably beautiful, so it deserves their attention.

113 Great Buffalo Trace, Frankfort   

Back in Louisville, the bartenders at Frankfort Ave. Liquor and Wine are not a particularly bubbly bunch, and that’s fine for customers who don’t need a lot of chitchat at the bar. Sometimes you just want to nurse a glass of Pappy Van Winkle 12 Year in peace. 

Frankfort Ave. Liquor and Wine co-functions as a liquor store and bar, and the staff can provide expertise in choosing both a cocktail to drink and a bottle to take home. Frankfort Ave. also specializes in rare bottles, and it mixes some of the most elegant craft cocktails in town. Bourbon neophytes can skip the overwhelming selection and simply get a Bourbon Slushie—and yes, that can be taken to go, just like all of the drinks here. 

When Frankfort Ave. isn’t hosting bourbon tastings, local bands play in the front of the shop, and regulars on barstools chat with new customers as they drop by. Be sure to say hi to Atticus, pictured above, who stops by most days.

2115 Frankfort Ave., Louisville   

Southern hospitality? You won't find much of that at Proof on Main. This place is too stylish to bother with that. The staff at Proof on Main tends to sigh, roll their eyes, and respond “No worries” to touristy questions that aren't worrisome anyway. This is the place to see and be seen for Louisville’s A-list, where exquisitely crafted cocktails are created from a massive list of Kentucky bourbons, ryes, whiskeys, whiskys, and every other elegant spirit in the cocktail world. The cool kids drink Paper Planes, a mix of bourbon, Aperol, and just a splash of social privilege.

Proof on Main occupies the front of the 21C "museum hotel" lobby, a stylish and comfortable hotel (and another overnight option, if it’s your scene) that houses an impressive contemporary art gallery. It’s easy to find: Just look for the giant golden statue of Michelangelo’s David on Main Street.

700 W. Main St., Louisville