If you’re planning a trip to an unknown city, you generally want insight from a trustworthy local. A seasoned veteran. An expert.
So when I found out I would be visiting Lexington, Kentucky—a.k.a. the horse capital of the world—I was tickled pink to learn that an actual horse named Oliver would be handling my itinerary. After all, who better to do the job?!
Oliver isn’t just any horse; he’s part of Lexington’s new Neigh-I experience, the world’s first horse-powered travel planner, featuring an actual horse that will plan your trip from A to Z. In a world where AI ‘reins’ supreme, Lexington decided to horse around with its own equine alternative to artificial intelligence in honor of the city’s 250th anniversary.
So, how does it work? Well, it’s actually quite simple. Travelers will first answer a few quick questions online, then Lexington’s trusty local expert, Oliver, will curate the perfect itinerary by noshing on carrots, apples, peppermints or other treats associated with his picks. Don’t believe us? See here for the low-tech, highly adorable process.
Once Oliver did his thing, I saddled up and spent 72 hours in Lexington, putting all of my faith in his talents. And, you know what? He did not disappoint.
Experience small town charm with big time hospitality
Walking around Downtown Lexington, you just may be compelled to throw on a feel-good playlist and skip through the streets because it’s cute as hell. With bright, vibrant wall art and small, local shops with inviting storefronts, you’ll feel as though you’re on a movie set. Strangers will wave and smile at you on the street, so consider this your warning: you may experience the warm-and-fuzzies.
But all that said, Lexington is more than just a sweet little town. From the moment we checked into The Manchester, our boutique hotel in the heart of the distillery district, I knew that I was in a city that takes hospitality seriously. The décor alone had me snapping away at every inch of the lobby, and that was before I even laid eyes on the picture-perfect room and insanely aesthetic rooftop. Even if you’re not a guest, I highly recommend popping in for cocktails at the lobby bar, sunset drinks at Lost Palm upstairs or an indulgent brunch at Granddam on the ground floor.
Gain a new appreciation for horse culture
I have been around a horse or two in my day, and I’ve even ridden a few on previous trips. I’ll be honest, though, that was the extent of my understanding—until I set foot in the so-called horse capital of the world.
Lexington is home to hundreds of thoroughbred farms, where horse racing legends were born and bred, and these horses are (rightfully) treated like royalty. Take Mill Ridge Farm, nearly 1000 acres of pristine land where the world’s best racehorses have been raised since 1962. This family-owned operation has it all down to a science, and you can tell they pour so much love and care into everything they do.
We also had the chance to visit Keeneland, one of the world’s largest and most prominent thoroughbred auction houses that hosts world-class racing twice a year. It’s open to the public year-round and draws people from near and far to participate in the festivities.
The horse culture in Lexington is truly ingrained in the city’s DNA, and it’s something worth seeing firsthand.
Raise a glass to Kentucky bourbon
Aside from its horses, Lexington’s pride and joy has to be its bourbon. With 18 renowned distilleries and countless world-class bourbon bars in the area, this truly is a bourbon lover’s dream. If you’re looking to learn a bit more about America’s native spirit, or get a firsthand look at the process behind it all, Lexington is where it’s at.
Thanks to Oliver’s carefully curated itinerary, we had the opportunity to visit Bespoken Spirits, which crafts its own award-winning bourbons right in the heart of Lexington. This place is doing things differently, with innovative technology and advanced wood finishing to accelerate aging and create bespoke spirits that are helping redefine the industry.
Photograph: Dana Rozansky for Time Out
You can tour their cutting-edge facility to see where the magic happens, and end with a strong cocktail or a tasting of several spirits to send you on your way with a nice buzz. You can even customize your own bottle to commemorate the experience with the ultimate keepsake.
Come for the drinks, stay for the surprises
The coffee shops, wine bars and cocktail lounges in Lexington offer more than meets the eye. Take The Greenery, for example. At first glance, it appears to be a straightforward coffee shop. But step inside, and you’ll find groups of friends catching up, students studying, or people kicking back and watching a movie that’s playing on a projector in a cozy nook. It’s a bustling social space that’s a hub for “coffee, community and plants”—yes, plants. Walk outside and you’ll find yourself in a green oasis (hence the name), where coffee and conversation are flowing.
Another one of my favorite stops was The Willow, a women-founded collective that aims to foster community, creativity and connections. While that may seem like a string of pretty words, upon walking into this zen, welcoming space, they genuinely practice what they preach. This cozy wellness and wine bar is the ideal place to unwind, hang with a friend, or simply enjoy some R&R with a crisp glass of white.
At Trifecta, a unique spot where you can find glassblowing and an art gallery, I also stumbled on a speakeasy—all in one place. Business in the front, cocktails in the back.
Eat your way through town
It goes without saying that we spent a full 72 hours indulging in Lexington—from biscuits to deviled eggs to crab cake Benedicts and burgoo stew, a Kentucky delicacy. From lunch at Carson’s to dinner at Epping’s on East Side, we did not go hungry. But one of my favorite ways to experience the variety of delicious food options this town has to offer was the Bites of the Bluegrass Tour.
This tour involves the perfect blend of history, food and booze, so you can at least feel like you learned a thing or two while being an absolute glutton and lush. We opted for the Distillery District tour, which included visits to local distilleries, iconic pizza shops, craft ice cream stores, and a swanky speakeasy tucked behind a barcade. It was truly the whirlwind food-and-drink experience I didn’t know I needed.