The definition of bourbon is an argument I’ve had many times, inevitably over a glass of the spirit. “Bourbon can only be made in Kentucky,” they’ll argue. Not true. But I can understand where the point derived, seeing as how 95 percent of the world’s bourbon is produced in Kentucky, praised for its limestone-filtered water and climate conducive for aging, allowing the liquor to absorb the caramel, vanilla, and spice notes inherent in the wood. It is, in fact, an $8.6 billion industry for the state.

It is considered whiskey, but to be called bourbon, it has to be made with at least 51 percent corn; aged at no more than 125 proof in new white oak barrels for no less than two years; and bottled at a minimum of 80 proof. And unlike other whiskeys, there cannot be any additives, like honey.

But I didn’t come to know the finer points of bourbon just out of curiosity. I discovered a taste for bourbon and a deep fascination for its history and nuanced production through various excursions along the Kentucky Bourbon Trail.

Of the state’s 68 distilleries, 38 are members of the Bourbon Trail, most of which are concentrated between Lexington, Bardstown, and Louisville (that’s LOO-a-vul in native speak). Distillery tours, tastings, and experiences like cocktail classes nurture a deeper appreciation for the spirit. In close proximity are bars and restaurants serving a dizzying array of labels and bourbon-tinged bites. There are museums detailing the history, cooperage tours focused on the art of barrel-making, and a handful of companies offering safe transport. Factor in the opportunities for exploring Lexington as the Horse Capital of the World, Louisville’s vibrant urban offerings, and the rural countryside in between—particularly lovely in autumn—and it’s hard to know where to begin an excursion.

Thankfully, the official Bourbon Trail website is a well-organized resource. Though speaking from experience, I like approaching the trail over a long weekend, or up to a week if time permits. In any case, tackling three distilleries per day is manageable, and it’s nice to mix up visits to the larger heritage brands—names like Jim Beam, Wild Turkey, and Maker’s Mark—with some of the smaller craft distilleries. Though the process of making bourbon doesn’t vary widely, the tours and knowledge gained at each is individual, as are the hours and fees.

I begin my trip, a four-day girls’ getaway, with two nights in Lexington. More time would allow exploration of the expansive Kentucky Horse Park to learn about the history of horses and meet retired Derby winners, or hone my betting game—mint julep in hand—at Keeneland, a handsome, historic stone track that, in a normal year, hosts horse races for three weeks every April and October. 

Arriving in the afternoon, we check into the chic 21c Museum Hotel and set off for the in-town distilleries. There are four in the city proper, all in close proximity. The James E. Pepper Distillery is a fitting place to start, as its storied history is as old as bourbon itself. Founded in 1780 by the Pepper family, it was once the country’s largest whiskey distillery, and the Old Fashioned cocktail is rumored to have been invented in honor of Colonel Pepper himself. 

Armed with a foundation on production and short on time, we opt to skip the Barrel House Distilling Co., located in the same historic complex, to head a mile away to Town Branch, named for the limestone-rich waterway that once drew distillers to its banks, but has been buried under the city for more than 100 years. This one’s a shorter tour, only 30 minutes, though an hour would’ve included insight into their brewing operation, which produces bourbon-barrel-aged ales.

Primed to sample more bourbon, we dine at Lockbox, located inside our hotel, which is also a museum. Amid the contemporary art hanging on stark white walls and ultra modern décor, we dine on elevated seasonal Southern fare while sampling flights from a menu of 170 bourbons. Some 25 distilleries are represented, so we take our server’s recommendations, opting to sample from those not on our itinerary.

Day two involves several distilleries in the countryside west of the city. We start at Buffalo Trace, which is not a member of the trail, but unlike other distilleries, the tours here are free. The sprawling brick complex reminiscent of the industrial era is the oldest continuously operating bourbon distillery in the country. Take in one or more tours here to learn how its many fine bourbons, including Pappy Van Winkle, are produced. Blanton’s Bottling Hall, where each single-barrel whiskey is bottled by hand, is particularly memorable. We grab lunch at the on-site Firehouse Sandwich Shop before heading on.

Unique in its Spanish Mission-style architecture, Four Roses was built in 1910 and is listed on the National Register of Historic Places. The tour here covers the romantic marriage proposal that inspired the name as well as the fermentation and distillation process. (The aging and bottling facility is an hour away and also offers tours.)

We bypass Wild Turkey—worth visiting for its award-winning visitor center—and head on to Woodford Reserve, which is idyllic, as is the drive there, past white-fenced horse farms and rolling hills. From fermentation and distillation to storing and aging to bottling and tasting, the tour of the historic stone distillery is top-notch and the products exquisite. Ending our day of small sips, we fill up at the Stave Restaurant and Bourbon Bar nearby, sampling the pulled pork with bourbon-peach barbecue sauce.

Heading on to Louisville for two nights, we take in Bulleit distillery, discovering the virtues of their bourbons and spicier rye whiskey (made from at least 51 percent rye grain) before heading into the city to check into the graceful historic Brown Hotel—within walking distance of many points of interest and where the sinfully decadent Hot Brown sandwich was invented.

Louisville’s Whiskey Row is a block-long stretch of Main Street that was once the thriving heart of the city’s bourbon industry. Many of the Revivalist and Chicago School–style buildings from the mid- to late-1800s have been restored, and, today, in and around the district are a plethora of distilleries, restaurants, and bars.

We take in Old Forester Distillery, which is unique in that it houses an on-site cooperage where you can watch the barrels being made and charred. Savor small-batch bourbon truffles at Art Eatables, and gawk at the impressive displays—including one on the history of Whiskey Row—at the Evan Williams Bourbon Experience.

Our final day on the trail, we make the 30-minute drive south to Jim Beam. Guests can tour and taste in downtown Louisville at their small distillery and bottling line Urban Stillhouse, but we opt to see the main operation for the full tour as well as a cocktail class, where we learn the art of an Old Fashioned and enjoy a lunch at the on-site smokehouse.

Back in town, we can’t decide between a tour of Angel’s Envy or the new and very modern Rabbit Hole distillery, but opt to rest up instead before venturing out for a bar crawl along the Urban Bourbon Trail, which encompasses more than 40 bars and restaurants. From the Old Seelbach Bar, where the likes of F. Scott Fitzgerald and Al Capone were known to frequent, to the underground Pin + Proof speakeasy and vintage bowling alley, we savor flights, cocktails, and snacks, glad not to worry about driving.

Dinner at Bourbons Bistro is the highlight, where we crown our meal and weekend adventure with an amazing bourbon bread pudding and smooth glass of Noah’s Mill from Kentucky Bourbon Distillers in Bardstown. Though we must head home in the morning, we savor our nightcap with a toast, promising to return for more bourbon exploration.


21c Museum Hotel A boutique hotel group that houses a contemporary art museum and restaurant. Even the public restrooms push the boundaries of art. 

The Brown Hotel This gilded Georgian-Revival hotel is a historic landmark with a AAA Four Diamond rating. 


Kentucky Bourbon Festival Normally held in mid-September in Bardstown and currently scheduled for October 15–18, 2020, this festival presents dozens of events centered around bourbon. 

Urban Bourbon Trail Louisville boasts just over 40 bourbon bars and restaurants on the Urban Bourbon Trail—a chance to put your taste buds to the test.


Lockbox This modern, artful restaurant serves elevated seasonal Southern fare and a bourbon menu topping out at 170 labels.

The Stave This relaxed restaurant and bourbon bar serves Kentucky standards like burgoo, a stew with chicken, pork, beef, and veggies, as well as Hot Brown Tots, a twist on the traditional Kentucky sandwich doused in savory cheesy Mornay sauce, along with a lunch and dinner menu of tasty Southern dishes. 

Bourbon’s Bistro Housed in an 1870s building, Bourbons Bistro offers a selection of 130 bourbons and a seasonal menu that’s locally sourced and inspired by its namesake beverage. 

Due to the COVID-19 pandemic, some distilleries are currently closed or operating on a reduced schedule, with safety measures in place. Reservations for tours (operating at a lower capacity) are highly recommended and in some cases required. Most tours, which include a tasting, cost around $10–$20 and take an hour. Visit for trip planning essentials, but be advised to check individual distillery websites for up-to-date hours and details.