Venturing out to the distilleries of central Kentucky can feel like a scene from a cowboy movie: fields of wheat and hay whip past, and then you pull into a gravel lot next to a pasture filled with glistening thoroughbreds and climb out of the truck. Inside a huge building filled with leather sofas, you are greeted by the occasional roaring fireplace or bronze statue. Soon, you’ll be whisked away to learn about a group of pioneering Americans who started out on the frontier – when the city was nothing more than a tavern and a port – all in pursuit of the treasured liquid we call whiskey. It’s the kind of spectacle you’d expect from the distilleries along the Bourbon Trail; and in certain parts of Kentucky, dotted with whiskey-makers and their wooden rickhouses, it’s exactly what you’ll get.
The Kentucky Bourbon Trail is like a cocktail with a base of frontier heritage, mixed with American ingenuity, shaken three times and poured over a huge rock of Southern hospitality. At its centre is the juice that made the area famous. When the Bourbon Trail was founded in 1999, with just seven venues, all the distilleries offered rustic charm – an aesthetic somewhere between opulent steakhouse and homespun country retreat. The bourbon barons of pre-Prohibition Kentucky were among the wealthiest people in town, but they weren’t city folk, and they made sure you knew it. Whiskey has since grown beyond these traditional settings, though: today, there are more than 100 distilleries in bourbon’s motherland, and the Bourbon Trail showcases 46 of them.
Nevertheless, some of these so-called newcomers are bringing the most historic stories to light. Castle & Key in Frankfort joined in 2022, after reopening the original 1887 castle based
distillery where EH Taylor Jr, the ‘father of the modern bourbon industry’, made his world-renowned whiskey. ‘It’s a great first stop, because you can learn about what it was like to
build a bourbon business. Plus how the distilleries eventually got into trouble because of debts and Prohibition,’ says Jack Beguedou, a US-based whiskey expert and content creator. Even without the history lesson, it’s a stunning introduction to the trail, walking the gleaming wooden floors of a fully restored limestone castle studded with arched windows inspired by the more historic fortresses of Europe. If the setting puts you in any doubt of your location, the biscuit dough, creamy honey and warming cinnamon-spice notes in Castle & Key’s Small Batch Wheated Bourbon Whiskey will feel like a proper Southern hug.
‘In Kentucky, bourbon is a way of life,’ says Edward Lee, who owns two restaurants – 610 Magnolia and Nami – in Louisville, Kentucky’s largest city. For chefs such as Lee, bourbon goes beyond the glass as an ingredient in high-end and homely cookery. To Kentuckians, bourbon is the smile-making, job-creating, celebration-worthy motivation for more than 2.5 million visitors to pour into the state each year.
The Kentucky Bourbon Trail is like a cocktail with a base of frontier heritage, mixed with American ingenuity and poured over a huge rock of Southern hospitality
In 1783, before Kentucky was even a state, Evan Williams established a distillery on the banks of the Ohio River. That waterway was essential to the growth of whiskey in the region, acting as the pre-railway connection to trading ports and commerce. Water is also the lifeblood of bourbon, accounting for about 50% of the liquid. Here, water trickles through limestone aquifers that naturally filter it, adding the right minerals to make the lively bourbon for which Kentucky is known. This water also fortifies horses’ bones, making them strong enough to carry 450kg of muscle (and just about 54kg of jockey) around a racetrack.
‘If you’re coming to Kentucky, there are two things you have to see,’ says Beguedou: ‘bourbon and horses. Even better if you can see them together.’ Along the Bourbon Trail, you’ll find hundreds of horse farms and two internationally acclaimed racetracks. To the east, the country’s most prominent thoroughbred auction house and racetrack, Keeneland, sits just 20 minutes from the downtown area of Lexington, Kentucky’s second-largest city. One of the finest hotels there, The Manchester, offers private polo lessons and has an equestrian theme weaving through the luscious rooftop bar and the design features of each suite.
Then there’s the iconic Churchill Downs, home of ‘the most exciting two minutes in sport’, the Kentucky Derby. Each year since 1875, on the first Saturday in May, crowds have flocked to the elegant event dressed in their finest, clutching a Mint Julep, the race’s official drink. There’s a certain delight in a tradition tied to the same place for 150 years – similar to dusting off a century-old bottle of bourbon.
While expressions that are as old as the Derby are scarce, you can find decades-old bottles at Bluegrass Tavern in Lexington, Neat Bourbon Bar in Louisville or Toogie’s Table in Bardstown. Bardstown Bourbon Company has a spectacular, hard-earned selection of pre-Prohibition whiskey available by the ounce; pours that are more than a century old start at $600. ‘Part of being modern is understanding where things came from,’ says master blender Dan Callaway. ‘We intentionally built this collection dating back to 1892 to be surrounded by history.’
On the first Saturday in May, crowds flock to the Kentucky Derby dressed in their finest and clutching a Mint Julep
While visitors to its vintage library room will be immersed in the past, elsewhere its surroundings are far from antique. Sleek glass walls soar more than five storeys over visitors’ heads to enclose state-of-the-art stills. A modern bar made from white marble and stainless steel greets tour guests. This modern aesthetic reflects the fact that ‘bourbon isn’t your granddad’s drink anymore’, in Callaway’s words.
Indeed, bourbon tourists are younger, spend more and stay longer than others, according to the Kentucky Distillers’ Association. Restaurateurs, distilleries and government officials are shifting to welcome this new generation of enthusiasts, with updated takes on whiskey experiences. Lawmakers made the first move in 2022, allowing distilleries to open one satellite tasting room. Many jumped on the opportunity to have a brand presence in downtown Louisville. ‘When you’re at the distilleries, there are rules that limit samples, because everyone is driving,’ says Lee. ‘The newer distilleries in the city have bars attached to them, so you can do the tour, then sit and have a nice cocktail. And there are plenty of restaurants and bars within walking distance.’
A casual saunter through downtown Louisville leads you to a Manhattan cocktail-making class at Angel’s Envy Distillery, a whiskey-blending workshop in Bardstown Bourbon Company’s tasting room, or a historic tour behind the landmark cast-iron facade of Michter’s Fort Nelson Distillery. The cocktail offerings of the ‘bourbon district’ surpass the classics. At Proof on Main, smoked cinnamon and alpine liqueur mingle in unexpected drinks, while the menu at Gertie’s Bar features wild concoctions like Buy the Ticket, Take the Ride, a drink that accents Old Forester 100 with Amaretto, salted peanut and cherry cola.
Flavours are expanding beyond typical American fare outside the cocktail shaker, too. Lee has run 610 Magnolia, a restaurant serving upscale, modern takes on Southern classics (think a BLT with bacon pâté and fois gras) since 2003. But 20 years later, he opened Nami, a modern Korean steakhouse showcasing a totally different style of cuisine. The menu ranges from thick wagyu steaks to crispy-skin snapper and crab fried rice. Across the state in Lexington, Distilled on Jefferson serves fusion dishes including oysters topped with sriracha and yuzu, alongside mains like porcini-rubbed fillet with Okinawa sweet potatoes. At Toogie’s Table, you’ll find elevated Southern dishes including caviar on devilled eggs.
Between indulging in high-end meals and bourbon-heavy experiences, there is plenty of culture. The 21c Museum Hotel Louisville houses a public museum with rotating contemporary exhibitions, and the floors above its galleries are a chic place to rest after a day of adventures. Just steps away, the Kentucky Center for the Performing Arts – home to the nationally renowned orchestra, opera and ballet – stands on whiskey row.
Kentucky’s capital Frankfort has recruited contemporary artists and restored historic works to curate a public-art walking tour of murals, statues and functional sculpture. The whiskey is never too far away, though, with a handful of distilleries within 20 minutes’ reach, including Wild Turkey, Glenns Creek and Whiskey Thief Distilling Co.
Visiting Kentucky, you get a sense of what it’s like to fill a new oak barrel with whiskey: here, fresh ideas mingle with centuries of tradition. Whether sipping bourbon at a restored castle, a Korean restaurant or the front row of a concert, today the historic and more novel thrive side by side.
Distillery tours and tastings
Castle & Key Distillery
Frankfort
You can stop by Castle & Key anytime during opening hours to see the historic distillery, but its grounds are best experienced on a guided tour. You’ll learn about the characters who built the castle and the current team that restored it to whiskey-producing glory – and, of course, sample bourbon in the process.
4445 McCracken Pike, Frankfort, KY 40601
Michter’s Fort Nelson Distillery
Louisville
It took the team at Michter’s eight years to restore this historic venue on Louisville’s whiskey row. The pride in each decision shows as the tour winds through pristine halls around iconic Pennsylvania stills. The bar offers a chance to see the distillery without a tour and enjoy some of the best classic whiskey cocktails in the city, all meticulously mixed by lauded bartenders.
801 W Main St, Louisville, KY 40202
Willett Distillery
Bardstown
Established in 1936, Willett is still family-owned and run, and its whiskeys are prized for their craft and rarity. The distillery campus has a quaint feel, like visiting the family homestead. The second-floor bar serves elevated small plates that make for an excellent midday meal.
1869 Loretto Rd, Bardstown, KY 40004
Woodford Reserve Distillery
Versailles
Tucked among the horse pastures on the Lexington side of the trail, Woodford Reserve presents a thoughtful and tranquil visit. The VIP Master Distiller Tour Experience offers just eight fans a two-hour, in-depth exploration of the historic distillery, along with its lab and grounds.
7785 McCracken Pike, Versailles, KY 40383
Restaurants and bars
Kitchen & Bar at Bardstown Bourbon Company
Bardstown
This stunning, modern restaurant has food worth planning a day around, including mainstays like Kentucky poutine with local sausage, and a rotating chef’s special made to fit the seasons. Save room for a dessert pairing, matching a limited-edition whiskey with a sweet treat.
1500 Parkway Drive, Bardstown, KY 40004
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610 Magnolia
Louisville
The constantly changing tasting menu here features inspired takes on Southern staples. Opt for the beverage pairing menu, which reaches beyond wine to make use of local breweries and distilleries. Reservations are required.
610 W Magnolia Ave, Louisville, KY 40208
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MeeshMeesh Mediterranean
Louisville
Having opened at the end of 2023, MeeshMeesh has already picked up a fair amount of hype for its Levantine small plates. Groups can also order shareable feasts, such as a full rack
of lamb, grilled and spiced to perfection. There are plenty of bourbon cocktails to accompany meals, and fresh ingredients like apricot and cucumber mix with Kentucky’s signature spirit.
636 E Market St, Louisville, KY 40202
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Distilled on Jefferson
Lexington
This is the epitome of Kentucky hospitality. A warm, high ceilinged dining room is adorned with a chandelier crafted from antlers, and the menu sees creative takes on Southern favourites. A rich and comforting she-crab soup is garnished with a corn scallion fritter topped with caviar.
157 Jefferson St, Lexington, KY 40508
distilledonjefferson.com
Hotels
The Manchester
Lexington
There is always something happening at Lexington’s boutique hotel – from bourbon pairing dinners held with local distilleries, to private polo lessons – but it’s hard to tear yourself away from the cosy, equestrian-themed interiors.
941 Manchester St, Lexington, KY 40508
themanchesterky.com
The Kentucky Castle
Versailles
Although unaffiliated, the Castle & Key Distillery is a short drive from this serene property modelled on a European castle. The tower suites feature a charming spiral staircase that connects an elegant sitting room to luxe bed chambers with unforgettable views of the surrounding countryside. The staff are dripping in Southern hospitality and cater to any need without interrupting a relaxing stay.
230 Pisgah Pike, Versailles, KY 40383
21c Louisville
Louisville
The chance to sleep in a contemporary art museum is unique, but 21c Louisville’s food, beverage and amenities also help set it apart as a memorable stay. The steam room is one of the best places in Kentucky to sweat out a day’s worth of bourbon (should you need to).
700 W Main St, Louisville, KY 40202
21cmuseumhotels.com/louisville
Activities and events
Louisville Orchestra
Louisville
The Louisville Orchestra’s annual calendar of events spans family-friendly jazz tributes and traditional classical music. The orchestra took home a Grammy in 2024 for Best Classical Instrumental Solo.
624 W Main St #400, Louisville, KY 40202
louisvilleorchestra.org
Art Eatables
Louisville
Chocolates become a tribute to distillers’ dedication to their craft at Art Eatables. Each truffle is carefully mixed to highlight the nuances of specific bourbons around the state. At the main shop in Louisville, guests can order a tasting flight alongside their truffles – the peak pairing of chocolate and whiskey.
631 W Main St, Louisville, KY 40202
arteatables.com/shop/smallbatchbourbontruffles/4
Frankfort Public Art Tour
Frankfort
Frankfort may be the state capital, but it’s home to fewer than 30,000 residents, meaning you can walk the entire town in a couple of hours. The self-guided tour includes historical monuments, modern functional sculptures, murals telling the story of both present and past Kentucky, and many hopeful depictions of a bright (and sometimes bourbon-filled) future.
308 St Clair St, Frankfort, KY 40601
visitfrankfort.com/art
Kentucky Bourbon Festival
Bardstown
Each September, bourbon lovers and makers gather in Bardstown to celebrate the beloved whiskey that keeps the area running. Three days of talks, tastings and dinners with more than 60 distilleries culminate in a relay race that has teams compete to roll 225kg barrels of bourbon with the bung facing perfectly skywards (just as they rest in the rickhouses).
114 N 5th St, Bardstown, KY 40004
kybourbonfestival.com
