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How Lexington, Kentucky, Landed On Our Travel Radar

Bourbon, horses, and rolling hills make for a very good time.

lexington kentucky city guide
A few years ago, when my cousin Nazera announced that she was accepting a job as an associate English professor at the University of Kentucky, I was both thrilled about her career move and surprised by where it was taking her. She grew up in D.C. and, like most of my cousins and I, has been drawn to big cities like New York, Philly, and Boston. “What is she going to do in Kentucky besides go to the Kentucky Derby once a year and watch college basketball? Does she even like college basketball?” These are the judgmental questions I asked myself; I’d never set foot in Lexington, but I assumed that it wasn’t all that exciting. I now stand corrected.

Back in April, my best friend and I hopped a flight to Lexington for the Land Rover Kentucky Three-Day Event (not to be confused with the Derby, which is held annually in Louisville). I know nothing about horses or equestrian competitions, and unless I’m at the beach or doing some al fresco dining and drinking, I generally prefer indoor activities. But the event was so fun! And the food in Lexington was so good! And the bourbon—wow. If you ever find yourself there or have the urge to book a trip, here’s everything I saw, ate, and did.


The Land Rover Kentucky Three-Day Event

lexington kentucky city guide
A mix of competitions, tailgating, and, for the truly committed, camping, the event draws elite equestrians from across the globe every April. It’s a qualifier for the Olympics, World Championships, and World Equestrian Games, so expect to mingle with lots of amateur and professional riders, and catch the three competition categories: dressage, show jumping, and cross-country. The cross-country course spans throughout the Kentucky Horse Park grounds, and you can see the action up close from the sidelines. Other highlights include shopping tents (there’s no better place to buy a pair of riding boots or a tweed jacket) and the Land Rover off-roading course, where you can drive the latest models up and down steep hills and through massive puddles. This year’s event will be held from April 25–28.

Distillery Tours

Approximately 95 percent of the world’s bourbon is produced in Kentucky, so there are a lot of options to see how it’s made, taste different varieties, and stock up before you head home. I visited Buffalo Trace Distillery, where a one-hour tour walks you through barrel-filled aging warehouses, the bottling hall, and a tasting room. Other distilleries in and around Lexington include Woodford Reserve, Wild Turkey, and Town Branch. [Note: I wasn’t stumbling back to the hotel afterwards, but unless someone in your group is going to skip the tasting, arrange for transportation, which many distilleries can help you coordinate.]

Small-Town Charm

lexington kentucky city guide
Among Lexington’s neighboring areas is Midway, population 1,800. A stroll down Main Street is a must. Start with coffee and homemade pastries at Higher Grounds on Main (I recommend the fresh cinnamon rolls), swing by Commotion for equestrian consignment finds, and browse jewelry, glassware, and gifts at Fisher Antiques.

More Bourbon

Mint juleps and old-fashioneds abound in this bourbon-enthused town, which is home to a thriving bar scene. For a speakeasy vibe, head to the Art Deco-influenced Parlay Social. If you’re really into bourbon, Bluegrass Tavern has 450 on the menu. Looking to relive your college glory days? Two Keys Tavern is the quintessential university bar, serving $1 wells on Monday nights if that’s your scene (no judgment).

Dine Out

lexington kentucky city guidePhoto: Courtesy of Instagram/@lockboxlex
I had the best meal of my trip at Lockbox, where Jonathan Searle whips up braised short ribs alongside hash browns and parsnips, and seafood dishes like scallops with red cabbage and simply grilled trout. Definitely save room for the sweet potato donuts. I didn’t get a change to try any barbecue, another Lexington staple, but everyone told me that I needed to visit Blue Door Smokehouse. I’ll be back for the ribs.

Top photo: Courtesy of Kentucky Three-Day Event  

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