Gainseway Farm
Driving south into Lexington, Kentucky on Interstate 75, you pass Kentucky Horse Park and International Museum of the Horse right at the city line. Enter from the west on Old Frankfort Pike, and you travel by the famous Secretariat statue. Fly into Blue Grass Airport and you’ll exit on Man O’ War Boulevard and drive past Keeneland racetrack. It’s pretty hard to miss the equine theme, which is why Lexington’s trademarked nickname is Horse Capital of the World. But the city also anchors the eastern end of the Kentucky Bourbon Trail, and it’s surrounded by distilleries, along with new experiences for whiskey lovers. You no longer need to leave the city to visit distilleries.
Lexington is only about half the size of Louisville, which lies around 80 miles to the west. But this vibrant city has been playing catch-up to its bigger rival in recent years, adding hotels, tours, attractions, and new distilleries. Resurgence is in the air, so if you’ve never been or haven’t visited in a while, it’s definitely worth a trip.
There are several good tour operators based in Lexington, like Distilled Experiences and Horse and Barrel Tours that offer private tours. Most operators have the option of distillery tours, horse tours, or a mix. Even if horse racing isn’t your thing, a visit to one of the horse farms is a fun and educational experience—more thoroughbreds are bred here than anywhere else in America. Many of these venues provide the opportunity to actually see some past Triple Crown winners.
Since Lexington isn’t a small town, big attractions like Keeneland racetrack and Kentucky Horse Park are nearby, so it’s possible to get around via rideshares such as Lyft and Uber, while the most popular major distilleries outside Lexington are 20-25 miles away. There are also some in the city itself now, and Lexington’s marquee urban attraction, the Distillery District, can be enjoyed entirely on foot.
Day One
No trip to Lexington is complete without a visit to the aforementioned Keeneland, one of the most iconic racetracks in the world. A National Historic Landmark, the track has twice hosted the Breeders’ Cup, and was the set for much of the movie “Seabiscuit,” as well as a stand-in for Belmont in “Secretariat.” Live racing meets are only held in April and October, but the track and extensive grounds are open for self-guided visits (they offer detailed maps) and more elaborate guided tours almost every day of the year. The hour and a half Backstretch Tour is offered from April to October with a look inside the barns, while the one-hour Morning Works Tour takes place year round, mixing a behind the scenes look at track operations with the horses’ morning on-track workouts. One of the best-kept secrets in Lexington is breakfast at Keeneland Track Kitchen, serving from 6 a.m. daily. View the historic collection of racing photos on the walls and rub elbows with jockeys, owners, and trainers while fueling up on the inexpensive cafeteria-style buffet featuring Southern specialties like grits and biscuits with gravy. You can also watch the morning training session from your table.
If you go during the track’s spring or fall meets, you can try a signature Keeneland Breeze (Maker’s Mark bourbon, orange liqueur, and ginger ale) and spend the entire morning at the track, but either way, the afternoon is perfect for visiting a distillery or two and a horse farm. You can sign up for a half-day tour with one of the tour companies or do it solo. Two of the most popular day-trip distillery tours are Castle & Key near Frankfort and Woodford Reserve in Versailles, both approximately 35 minutes from Lexington and less than a 10-minute drive from each other.
Castle & Key offers a choice of light snacks such as charcuterie and chips, plus neat whiskey pours, wine, and craft beer in the former distillery train station. You can also visit a seasonal food truck on the grounds. As the successor to the Colonel E.H. Taylor Distillery, built in 1887 to accommodate visitors, Castle & Key claims to be the first in the nation designed for tours, with its flagship European castle design and extensively landscaped grounds and gardens. This birthplace of bourbon tourism closed in 1972; renovations began in 2014 and its first new whiskey, Restoration rye, was released six years later, followed by bourbon in 2022 (they also make gins and vodka). There are hour-long tours ($30) daily, including a draft cocktail, and there’s no charge for exploring the grounds, shops, bar, and nature trails. This is one of the best distillery visits in the region.
Woodford Reserve offers a 30-minute guided tasting of five whiskeys ($25), a 70-minute comprehensive guided distillery tour with bourbon tasting ($32), the same tour with more extensive tasting ($125), an Old Fashioned-based mixology class ($40), and a 2-hour VIP experience with master distiller Elizabeth McCall or master distiller emeritus Chris Morris that includes a souvenir bottle ($500).
There are more than 400 horse farms in the area, and several offer tours. One of the most popular is the 3,000-acre Claiborne Farm in Paris (35 minutes from Lexington), where Queen Elizabeth visited in 1984 while on one of a number of trips the thoroughbred-owning monarch made to Kentucky during her long reign. Claiborne has produced hundreds of champions, including 10 Kentucky Derby winners, and is home to one of the area’s most visited attractions, Secretariat’s gravesite. A variety of tours are offered daily ($11-$30).
When you get back to Lexington, check out the new Fresh Bourbon Distillery tasting room in the heart of downtown, which debuted in 2022. Fresh has been recognized by the state of Kentucky as the first African American-owned company to make bourbon since slavery, and until its own facility is completed, it’s contract distilling at Hartfield & Co. Distillery in nearby Paris. Guided tastings with food pairings and mixology demonstrations are available (book in advance, $25).
Among the city’s top hotels is the art and whiskey-centric 21c Museum Hotel, a great choice for lodging and for dining. Its Lockbox restaurant is a standout and features a contemporary gourmet take on Southern cuisine, with an emphasis on sourcing from local family farms and other artisan producers (plus 24-hour room service). The bar serves one of the city’s most popular Old Fashioneds, with Old Forester and a special twist, parsley syrup, along with tasting flights and four private barrel selections (Woodford, Maker’s, Rebel, and New Riff ). Other good options include Manchester and Origin Hotels.
Day Two
Close to 21c, Doodles Breakfast & Lunch is a local favorite that serves American and Southern breakfast classics “with a conscience,” using many organic and locally sourced ingredients. There are lots of healthy options in addition to regional favorites like bacon beignets and Kentucky Hot Brown quesadilla. Worth a stop and just a few blocks away is Justins’ House of Bourbon (there’s one in Louisville too), with lots of rarities, exclusive bottlings, and a museum-like selection of very old bottles for sale, some pre-Prohibition. Justins’ also has a bar that offers tastings to help you select purchases, plus paid samplings of more exclusive bottles. Liquor Barn is another area retailer known for its expansive bourbon selection, including pricey, hard to find bottles like Jefferson’s Marian McLain blended straight bourbon and Hirsch cask strength bourbon finished in XO cognac casks, as well as more affordable labels, with multiple locations in and around the city. If you are flying non-stop out of Lexington’s Blue Grass Airport, you can shop Cork & Barrel’s large collection of Kentucky bourbons and carry them right onto the plane.
Next, head to Kentucky Horse Park, whose state fairgrounds atmosphere includes four museums, barn tours, horse-drawn carriage rides, statues, gardens, and the Hall of Champions, where retired stars—including Kentucky Derby and Preakness winner Funny Cide and Belmont Stakes champ Point Given—now live.
Afterward, it’s time for Lexington’s Distillery District. This 25-acre pedestrianized neighborhood occupies the site of the 1879 James E. Pepper Distillery, which was abandoned for half a century before a massive 2008 renovation. It now has two working distilleries: the reborn version of Pepper and Barrel House Distillery, producer of RockCastle and Barrel House bourbons. The Pepper tour visits the distillery and museum, and includes a tasting ($20), while the guided Barrel House tour and tasting is $10. There are many good choices within the Distillery District for lunch, including the Elkhorn Tavern at Barrel House, with regional specialties like pulled pork and pimento cheese sandwiches and burgoo, a traditional Kentucky stew, plus signature whiskey cocktails like the Elkhorn Smash (Barrel House bourbon, pinot noir, cherry, lemon, and simple syrup). The District also contains a craft brewery, Ethereal Brewing, and a cidery, Wise Bird Cider. There are additional bars, restaurants, and shops, a live music venue, bocce courts, and even axe throwing.
The biggest recent addition to the Lexington tourism scene is the Distillery District’s first hotel, a good place to stay and a great choice for dinner. The Manchester opened in early 2023 and was designed to reflect the style of historic whiskey rickhouses and horse barns, with the works of local artists displayed throughout. The Granddam restaurant serves upscale, farm-sourced versions of classical Appalachian dishes and has a patio for al fresco dining. There is also an Art Deco rooftop bar and lounge, Lost Palm, with a tiki cocktail program and tropically inspired island dishes. The hotel has a private cask program with Castle & Key, and signature Mint Juleps are prepared tableside with private label rye, rhubarb, and fresh fruit pearls. The whiskey list is global but focuses on Kentucky, and it’s a long one. The second-largest city in Kentucky is not second-rate for whiskey lovers.
Distilleries, Brewery, & Cidery
Barrel House Distillery 1200 Manchester Street; barrelhousedistillery.com
Castle & Key Distillery 4445 McCracken Pike, Frankfort; castleandkey.com
Ethereal Brewing 1224 Manchester St.; etherealbrew.com
James E. Pepper Distillery 1228 Manchester Street; jamesepepper.com
Wise Bird Cider 1170 Manchester St.; wisebirdcider.com
Woodford Reserve Distillery 7785 McCracken Pike, Versailles; woodfordreserve.com
Bars & Restaurants
Doodles Breakfast & Lunch 262 N. Limestone; doodleslex.com
Elkhorn Tavern 1200 Manchester St.; barrelhousedistillery.com
Fresh Bourbon Distillery Tasting Room 377 E. Main St.; freshbourbon.com
Granddam 941 Manchester St.; granddamky.com
Keeneland Track Kitchen 4201 Versailles Ave.; keeneland.com
Lockbox 167 W. Main St.; lockboxlex.com
Lost Palm 941 Manchester St.; lostpalmky.com
Hotels
21c Museum 167 W. Main St.; 21cmuseumhotels.com
The Manchester 941 Manchester St.; themanchesterky.com
Origin 4174 Rowan; originhotel.com
Tours
Distilled Experiencesdistilledexperiences.com
Horse and Barrel Tourshorseandbarrelexperiences.com
Attractions
Claiborne Farm 703 Winchester Rd., Paris; claibornefarm.com
Keeneland Racetrack 4201 Versailles Rd.; keeneland.com
Kentucky Horse Park 4089 Iron Horse Pkwy.; kyhorsepark.com
Lexington Distillery Districtlexingtondistillerydistrict.com
Shops
Cork & Barrel Blue Grass Airport; lexcorkandbarrel.com
Justins’ House of Bourbon 601 West Main St.; thehouseofbourbon.com
Liquor Barn 4131 Towne Center Dr.; liquorbarn.com
