Adventures on the Kentucky Bourbon Trail

Last year, nearly 1.2 million people visited the Bluegrass State to explore the Kentucky Bourbon Trail, an excursion many liken to Napa Valley at a higher proof. Through the rolling hills of central Kentucky, the historic distilleries of more than a dozen top-shelf bourbon brands and many more artisanal upstarts open their doors every day to those looking to experience from its source the amber nectar that has contributed to American drinking culture since the dawn of the republic.

In the pre-Revolution days, most of the liquor consumed in the original 13 colonies was rum produced from sugarcane in the British West Indies. But during the war, British naval blockades forced Americans to find a drink made closer to home. Distilleries making fruit brandies and whiskeys from native grains like corn and rye popped up all along the East Coast, including at George Washington’s Mount Vernon estate. So why did Kentucky whiskey survive the test of time? And why is it called bourbon, anyway?

The answers to both of those questions begin at the river. Before the dawn of the steam engine, waterways were the only means to get a product like whiskey to market. And Kentucky, being the first state in the Union founded to the west of the Appalachian continental divide, had the longest route to market. Distilleries in the east were either in port cities or just a few days by river from a port city, which meant the whiskey made there was sold for consumption without any delay. Kentucky distillers, on the other hand, had to wait for spring rains to raise the rivers enough to float their flatboats loaded with barrels. From there, it took at least two months to make it downriver to the port of New Orleans.

During that long journey, the whiskey would slosh around in its charred oak barrels, which mellowed the taste and gave it color. The barrels were burned not with the intention of imparting deeper flavor, but rather to eliminate whatever flavors were already in there before they were filled with whiskey. Industrious pioneers in the Kentucky wilderness would take barrels used previously to store anything from nails to salted fish or pickles and torch the interiors to remove the remnants of previous tenants. Those charred vessels were filled with liquor and sent downriver, and when they were finally opened in New Orleans, the whiskey inside tasted better than anything they could make on the bayou.

For bookkeeping, Kentucky distillers branded each barrel with its county of origin. Bourbon County, founded in 1786, was one of the state’s five original counties, named in honor of the family of the Marquis de Lafayette to celebrate his role in the American Revolution. (The county seat in Bourbon is the town of Paris for the same reason.) And so the smoothest, darkest whiskey of the New World became known to New Orleans drinkers by its stamp, a name that was already familiar to French-speaking cajuns who had named a whole street for the Bourbon family just a few blocks from the river. The first documented example of Kentucky whiskey being referred to as “bourbon” comes from Louisiana in 1855.

By the end of the Civil War, railroads had taken over transportation from the riverboats, making those months-long floats to market unnecessary. But Kentucky distillers soon developed a warehousing method to age their bourbon, using charred white-oak barrels to replicate the process. It’s how the state became the home of the bourbon industry, and it’s the reason more than a million people per year can’t resist its call.

The idea of opening distilleries to the public goes back 50 years to Maker’s Mark, which was started as a modest family business by Bill Samuels Sr. in 1950. In 1968, Bill’s daughter, Leslie Samuels, opened a visitors center in the old distiller’s house on the property, making it the first official tourist-friendly distillery in the country. At the time, Maker’s was also the only premium bourbon around—Kentucky whiskey was mostly associated with rough-and-tumble saloons. But Samuels was smart, advertising in high-end publications like The New Yorker and The Wall Street Journal. By 1980, Maker’s had become the first distillery in America to be designated a National Historic Landmark. And as it rose from upstart to market leader, old-school distillers began to replicate its success. Brown-Forman reopened its dilapidated distillery in Woodford County and began making Woodford Reserve; in 1994, Jim Beam released its signature collection, a new batch of premium brands like Knob Creek and Booker’s—the first bourbon bottled at a barrel strength of about 126 proof and named for Booker Noe, the longtime master distiller of Jim Beam.

The job of master distiller is to maintain the consistency of a whiskey’s flavor over time, and the only way to do that is with a flawless palate—taste buds as acute as the ear of a musician with perfect pitch—and Booker Noe had the gift. As the story goes, Booker once bragged at a dinner party that he could name any bourbon in a blind taste test. His hosts didn’t believe him, so he proved it by identifying a half-dozen different bourbons in a few sips. When they mixed several different bourbons together and served it to him, he tasted it, thought for a minute and said, “Somebody is trying to fool ole Book.” Before the release of the Booker’s brand, the role of the master distiller had been practically invisible to the public—now it was right there on the label.

Bourbon production has tripled over the last 20 years, and the $8 billion industry is booming—there are now more than 50 distilleries in the state, with a total inventory of nearly 7 million barrels of liquid gold aging to perfection at this very moment. The official Kentucky Bourbon Trail includes a consortium of commercial and craft distilleries that have banded together, and it’s by far the best entry point for any bourbon odyssey. The city of Louisville itself has also emerged as a hub, with its own Urban Bourbon Trail, complete with historic hotel bars, bourbon-inspired cuisine and new distilleries breathing fresh life into a centuries-old Kentucky tradition.

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— Maker’s Mark —

If you’re on a bourbon pilgrimage, Maker’s Mark is your Canterbury Cathedral—the farthest point out in the journey and one of the best places to start—it’s here that you’ll receive bourbon enlightenment. Of all the distilleries on the trail, Maker’s might be the most out of the way, tucked into a ridged landscape of sugarloaf hills and rolling knobs along winding, narrow country roads. Rescued from its post-Prohibition dilapidation by the Samuels family, the original compound of 10 buildings, built by descendants of Charles Burks in the 1880s, has been lovingly restored, expanded and improved over the years, with additions like an 8,000-square-foot cave for barrel storage, completed last year, carved directly into the temperature-cooling rock cliffs. The facility makes one of the greatest American spirits of all time, crafted in 19-barrel batches every day. A stone-walled creek runs through the meticulously groomed grounds, and the black buildings framed by bright red shutters—painted to reflect the color of a bourbon bottle and its red wax seal—are nearly as distinct as the smell of corn, wheat and malted barley cooking in the stills. The one-hour tours cost $12 per person and offer a complete look at each stage of the process, with an option to dip your own bottle in the trademark wax. You can also purchase special editions you can’t find at your neighborhood liquor store, like a barrel-strength variety, an unaged “white dog” for moonshine aficionados, and several expressions available exclusively on-site, like Bill Samuels Jr.’s Private Select, a seasonal offering from the distillery’s taste panel, and an iteration from the restaurant on campus, Star Hill Provisions, curated by chef Newman Mill.

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— Jim Beam —

The American Stillhouse at the original Jim Beam distillery in Clermont, Kentucky, is about 30 minutes south of Louisville and designed to welcome guests by the busload. The Beam experience takes you back to the 1790s, when early distillers like Johannes Bohm (later Americanized to “Beam”) and Basil Hayden traveled to central Kentucky with their stills in tow. One of Beam’s early brands, Old Grand Dad, was originally made by Raymond Hayden, grandson of Basil Hayden. Come for Beam’s high-end small-batch brands, like Knob Creek, Basil Hayden’s, Baker’s and Booker’s, but stay for the varieties of Jim Beam, like the eight-year-old black label, the double-barreled Double Oak, the deep flavor of Devil’s Cut and the retro cult classic: the orange-labeled Old Grand Dad, bottled-in-bond. Walk it off across the road in Bernheim Forest, a nature preserve with great day hiking and picnic spots.

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— Bardstown —

Between Maker’s Mark in Loretto and Jim Beam in Clermont is Bardstown, a bucolic hamlet built on bourbon. Visit the historic Talbot Tavern downtown at the roundabout and ask the bartenders what they like these days—then go around the corner to Toddy’s Liquor Store to see if you can find it. Here’s the secret to bottle hunting: You’re not going to find 23-year-old Pappy Van Winkle on the shelf at retail prices. In fact, it’s so rare that it can fetch more than $3,500 on the secondary market. But the deal is that every liquor store is given a stingy allotment of high-end, high-demand releases, sometimes just a bottle or two—and none of them ever make it to the shelf. The store owner keeps them in the back, and their best customers join a waiting list. So when you go into a place like Toddy’s in Bardstown, ask the person behind the counter what they’ve got hidden away for a customer who never came to pick it up. You might not get what you were hoping for, but you’ll probably get something excellent you’ve never tried before.

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— Heaven Hill —

Just outside Bardstown sits Heaven Hill, one of the original legacy distilleries on the trail and one of the few that remain family owned and operated. Its warehouses are perched on the last spit of flat land before the ring of wooded knobs that separates Bardstown from the wilderness beyond. While the name might not be immediately familiar, what’s inside surely will be. This is the home of two of bourbon’s forefathers: Evan Williams, the purported founder of the first commercial distillery in Kentucky, and Elijah Craig, a Baptist preacher credited as the first distiller to store his whiskey in a charred oak barrel, now an official requirement for all bourbon. While both of those claims might be up for debate, one thing is not: Whisky Advocate named Elijah Craig Barrel Proof its Whisky of the Year for 2017. These flagship Heaven Hill brands are backed up with a growing line of small-batch premiums, like Henry McKenna and Larceny, all available to sample at its Bourbon Heritage Center, which is as much a museum as a gift shop. Tours here start at $10 per person, where you can learn more about the history of Kentucky bourbon and the terrible fire that destroyed seven historic warehouses and 90,000 barrels of bourbon in 1996. It might have spelled the end for Heaven Hill, but instead the place has come back stronger than ever.

Less than a mile down Loretto Road is the newly refurbished Willett Bourbon distillery, a family-owned brand that dates back to 1936. Everything from the main distillery building to the cistern room, aging warehouses and turn-of-the-century belt and pulley fan systems have been completely restored. And right nearby is My Old Kentucky Home State Park, a preserved antebellum brick mansion said to be the inspiration for Stephen Foster’s classic song. In the summer there’s an outdoor theater production of The Stephen Foster Story, if you think you’d enjoy some early American songbook with your bourbon.

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— Lawrenceburg —

Wild Turkey has always been the bourbon with an edge because it’s bottled at 101 proof, a little stronger than its peers. Its distillery, with views of the Kentucky River from a perch at the top of the hill, packs just as much punch. The chances of bumping into spokesman Matthew McConaughey are low, but keep your fingers crossed for the opportunity to chat with master distiller Jimmy Russell or his son Eddie. Jimmy Russell is the last of his generation—the distillers responsible for bringing bourbon into its golden age—and he has amazing stories. For a taste of Spanish mission–style architecture in the heart of Kentucky, head down the street after to the unique Four Roses Distillery, built in 1910, which offers a limited tour schedule in the summer months.

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— Woodford Reserve —

As the only distillery on the Bourbon Trail in the section of the Bluegrass region known for its thoroughbred horse farms, Woodford Reserve might be the most beautiful property on the circuit, particularly for the verdant landscape that surrounds it, which is lined by stone walls and wooden fences and populated by more horses than people. The bourbon at Woodford Reserve somehow captures that Kentucky horse farm mystique, and on these grounds, brought back to life by parent company Brown-Forman, you can feel the 140 years of history. The 10,000-square-foot facility is designed to look old and beautiful on the outside and completely modern within. One-hour tours start at $15, with a more rigorous two-hour “Corn to Cork” tour for $30. Wednesdays are focused on the distillery’s early American frontier architecture, like the Woodford visitors center, built in the style of a 19th-century Shaker farmhouse with wooden siding, a limestone foundation and an inviting porch lined with rocking chairs. While the vast majority of distilleries in Kentucky are outfitted with copper stills from Vendome Copper & Brass Works in Louisville, the kettles at Woodford were imported from Scotland, which lends the place an old-world feel. The distillery hosts special events throughout the year, but especially on Friday nights in September, when they keep the tours running long, with live music and food to pair with your spirits.

• • •

— Frankfort —

The state capital can be a little sleepy if the legislature isn’t in session, but there are always tours available at the Buffalo Trace distillery, which is well worth a visit even though it’s not officially on the Kentucky Bourbon Trail. It’s the home of Pappy Van Winkle, the rarest and most coveted of all bourbons, along with other small-batch delights, like Blanton’s, W. L. Weller, Eagle Rare, Col. E. H. Taylor and George T. Stagg. There’s a long-running dispute with Maker’s Mark over whose distillery is older—Buffalo Trace claims to date back to the early 1800s—but both have plenty of history to go around.  

Also in Frankfort, and recently reopened after 42 years of neglect, Castle & Key Distillery is the hottest new thing in bourbon country. Its founders have invested heavily in the gorgeous 113-acre estate, replete with a European-style castle, sunken gardens and a distillery run by Kentucky’s first female master distiller since prohibition. And if you’re bottle hunting, Red Dot Liquor Store in Frankfort is a must-stop: Just ask them what they have in the back.

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— Louisville —

It’s easy to spend a whole weekend exploring the bourbon scene in Louisville, on the south bank of the Ohio River. From the lobby bars of the historic downtown hotels to upscale cuisine and stylish bourbon bars, it’s the home of the Old Fashioned, the Mint Julep and bourbon on the rocks. The Evan Williams Bourbon Experience is just a few years old; Jim Beam has opened an Urban Stillhouse at Fourth Street Live; and Moonshine University offers full courses on craft distilling, with one-day certifications to become a bourbon sommelier.

These days, you could make a whole trip of touring distilleries and never leave downtown, and something new seems to be opening every week. In June, Old Forester will christen its magnificent $45 million, 70,000-square-foot distillery on Whiskey Row—in a building it called home a century ago; Michter’s is in the final stages of saving and renovating the architecturally significant 1890s cast-iron Fort Nelson Building on Museum Row; bourbon pioneer Kaveh Zamanian just opened the doors to Rabbit Hole Distilling’s stunning and modern $15 million, 55,000-square-foot facility; and fellow upstart Angel’s Envy is now allowing visitors to bottle their own bourbon straight from the barrel for $99. Peerless Distillery, in a restored warehouse right up against the Ohio River, was resurrected in 2014 by Corky Taylor, whose great-grandfather had originally bottled Peerless Bourbon downriver in Henderson in the 1880s.

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— Bulleit —

In many ways, Corky Taylor at Peerless is following in the footsteps of Tom Bulleit. Another great-grandson of a distiller who relaunched his dormant family brand, he’s distinguished its whiskey with a frontier-themed bottle and a high-rye mash bill, which gives it a spicier flavor than most of its competition. In 2014, the success of the brand allowed Bulleit to reopen the abandoned Stitzel-Weller Distillery, just five miles south of Peerless, in downtown Louisville, lending them a platform on the trail in one of the industry’s hallowed halls. Originally known as the place where the rickhouse bourbon aging system was invented, in 1879, it was first resurrected in 1935, just after the repeal of Prohibition, and became famous as the legendary home of Pappy Van Winkle before closing again in 1972, forcing the Van Winkles to move their operation to Frankfort. Architecturally, the distillery is distinct from other spots on the trail for its brick-and-column Greek Revival flair, modeled after Thomas Jefferson’s Monticello.

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— Up River  —

Just up the Ohio River from Louisville in Crestwood, you’ll find the Kentucky Artisan Distillery, one of the great small operations on the trail and headquarters to Jefferson’s Bourbon, makers of Jefferson’s Ocean, which is aged at sea—the only bourbon with a salty flavor. A bit farther up the Ohio in Maysville is the Old Pogue Distillery, where a new generation of the legacy distilling family revived the brand in 2005.

At this point, you’ve definitely been drinking. But the good news is that you don’t have to get behind the wheel: Amtrak’s Maysville station is just a short walk down the street.