Sometimes the coolest towns can fly under the radar. Take Lexington, Ky.: the hometown of Richard Hell has quietly been one of the most interesting and entertaining places on the map for at least a few decades now. It’s a city defined by its region’s absolute dominance of two unique industries, bourbon and racehorses, and also by the University of Kentucky and its college basketball dynasty. But it also has the spirit of a college town, with the students at UK making sure it’s home to both a large bar and party culture as well as a thriving arts and music scene. From the races at Keeneland, to the distilleries on the Bourbon Trail, to the weird and unexpected sounds you’ll hear on WRFL 88.1 FM and in the city’s clubs and DIY spaces, Lexington will fascinate all manner of visitors, from first-timers to the super familiar. Here’s what you need to experience there at least once in your life.
It feels wrong to pick between bourbon and horses, but something has to go first, so let’s start with the booze. The official Kentucky Bourbon Trail runs throughout the state, and although the single greatest concentration of its 18 main member distilleries can be found in Louisville (which is about an 80 minute drive from Lexington), you can find four official Trail distilleries in and around Lexington, along with three additional distilleries that are part of the Trail’s Craft Tour. There are also Lexington-area distilleries that aren’t officially part of the Bourbon Trail, so there’s a lot of fresh bourbon to drink in this town. The biggest name among the bunch is Woodford Reserve, whose distillery in Versailles sits less than 15 miles away from Lexington. With a history that dates to 1812, and buildings that still stand from as far back as 1838, this National Historic Landmark will transport you back in time as you enjoy some of the best bourbon in the world. After over a century of producing bourbon, the site was closed in the late ‘60s, before the Brown-Forman Corporation bought it in the early ‘90s and reopened it as the home of the then-new Woodford Reserve. Today you can tour the grounds and see the giant vats of mash, the large copper stills in the still room, and the rows upon rows of barrels in the rickhouse, all within buildings from the 19th century. (The equipment is mostly new, of course.) Another historic distillery that has gained a second life can be found in Frankfort, about 27 miles from Lexington. Castle & Key sits inside a castle-style building that bears a sign proclaiming it “The Old Taylor Distillery Company.” Colonel E.H. Taylor, Jr., built the facility in 1887, and it was in operation all the way up to 1972 (except for a, uh, forced closure between 1920 and 1933). It sat empty for over 40 years, and despite its history and unique architecture it faced demolition until it was bought in 2014 by two partners who rechristened it as Castle & Key Distillery. (The “key” comes from a key-shaped well that provides the distillery with some of its water.) It’s a beautiful property that fully embraces its age, and a must-visit for anybody who likes cool old buildings or drinking.
One thing you’ll quickly notice around Lexington are the horse fences. They’re everywhere outside of downtown—a system of four-tiered, dark brown woodwork running parallel to almost every road. It’s tempting to call them the veins of Kentucky, as horses are definitely its blood. There are well over 400 horse farms in the Lexington area, and those horses have to be protected, not just from roaming outside of their paddocks but from any vehicles that might come flying off the road towards them. Those farms are home to mares, stallions, current racehorses, decorated (and highly lucrative) studs, retired legends, and more, and some offer official tours. Lane’s End, one of the top breeding farms, is home to almost two dozen stallions who are available to stud for prices ranging from $7,500 to $200,000; on a recent tour they brought a few of their top horses out for us to get a close-up view, and then introduced us to all the stallions in their stables. If you’ve ever wanted to get an inside glimpse at the unknowable high-dollar world of Thoroughbred breeding, you should look into a tour of Lane’s End Farm.
They don’t just breed, raise, and train Thoroughbreds in Kentucky, of course. They race ‘em, too. Keeneland, a National Historic Landmark, has been hosting meets for over 80 years; the track is home to races for over two weeks every April and October, a tradition that started in 1936. Although not as large or famous as Louisville’s Churchill Downs (the home of the Kentucky Derby), Keeneland is a gorgeous race course with a rich history of its own, and a perfect place to get your feet wet if you’ve never been to a race or bet on horses before. This year it was home to the Breeders’ Cup World Championships, one of the most prestigious races in the sport, and which, like the Super Bowl, doesn’t have a set annual home. Often called “the richest two days in sports,” every race at the Breeders’ Cup has at least a million dollar purse, so you’re guaranteed to see some of the very best horses in action. The people-watching is almost as exciting as the races, of course; women wear their flashiest hats while most men dress up to the nines with suit and tie. The Breeders’ Cup won’t be back at Keeneland for at least a few years, but every day at Keeneland is charming and exciting—and potentially very lucrative, if you play it right.
Even as a lifelong Tar Heels fan who earnestly believes that the ACC is the absolute best college basketball in the country, I have to acknowledge the historic greatness of the University of Kentucky’s team. Hell, they have the highest winning percentage in NCAA Division I history, and until earlier this year had spent over two decades as the record holder for total wins. You don’t get that by accident. Any fan of the sport should see the Wildcats in their native environment at least once, at the massive Rupp Arena in the heart of Lexington. Sure, UK has other sports, including a football program that often plays the spoiler against perennial SEC powerhouses, but basketball rules all at this school and in Lexington itself. And if you don’t care about basketball but still want to check out the legendary Rupp Arena, it hosts a variety of events throughout the year—including my niece’s high school graduation. As much as I loved watching our future take its first steps into the adult world, I think it probably would’ve been more fun to watch John Calipari’s team whip up on some unprepared SEC squad.
The Bars and Restaurants
During a recent trip to Lexington I balanced sophisticated farm-to-table restaurants in and outside the city with gloriously shaggy burger joints and dive bars that have been serving UK students for decades. One night featured a fantastic dinner at Epping’s on Eastside, where you can find delicious dishes like a pan fried fish marsala and a lamb shank birria and a rich variety of wines and bourbons. Hours later, after elbowing up to the hotel bar for a bit too long, and well past the point of making sound judgments, I found myself at the infamous Tolly-Ho, an all-hours burger and breakfast diner with cheap beer, cold milkshakes, and a 50-year history of winding down the night for local students and drunks. It’s no longer in the charmingly ramshackle building in which I first encountered it over 20 years ago, but Tolly-Ho still hits the spot, no matter how bad a decision it might be. The best meal of the trip came just outside Lexington, in the small, one-block downtown of Midway. A restaurant called Heirloom combines traditional downhome favorites with French inspiration, resulting in entrees like a sublime buttermilk-brined fried chicken, a hearty pork chop, and a duck breast with potato gnocchi that was my culinary highlight of the whole trip. Heirloom is a short drive from Lexington, but worth the trip. And no visit to Lexington is complete with a stop at the Chevy Chase Inn, a perfectly rumpled little dive that has been dishing out beer and bourbon for over 80 years. Expect cheap drinks, live music (a guitarist played country originals and classic covers on a recent Friday night), two great old pinball machines in various states of disrepair, and the comforting embrace of a bar that has presumably changed very little since my grandparents’ generation drank there.
There’s more to Lexington and its surrounding areas, of course, but this is what I can personally vouch for after a recent journey to the Horse Capital of the World. And although I sadly wasn’t able to find whatever constitutes the town’s current underground music scene, I’m sure the oversized college town that gave us noise icons Hair Police and the Elephant 6 band Ulysses, among others, has a number of great bands playing in homes, basements, and DIY spaces throughout the city. Whether you’re most interested in exploring the world of bourbon, seeing Thoroughbreds up close and in action, catching a basketball game, or eating some great food, Lexington, Ky., will have what you’re looking for.
Senior editor Garrett Martin writes about videogames, comedy, travel, theme parks, wrestling, and anything else that gets in his way. He’s also on Twitter @grmartin.