On the Road

Snapshot: Lexington, Kentucky

By: Robin Roenker

If you haven’t been to Lexington, Kentucky, lately, assume your visit is overdue. In the past two years, the city—despite being best known for its equestrian races and college basketball—has upped its culinary game in the form of a downtown dining renaissance.

Dozens of dining destinations that cater to any craving await within walking distance of famed Rupp Arena and adjacent to Triangle Park, where a picturesque waterfall fountain serves as a city center of sorts. They serve up the finest New York strip steak, avant-garde Italian, Latin fusion, or pizza and a craft beer. Use the city as a hub to explore the nearby Kentucky Bourbon Trail and iconic horse farms, or simply stay within the city limits to soak up this college town’s unique Southern charm.

What to Do in Lexington, Kentucky

Seating area surrounded by vibrant art and metal statues in Agave & Rye in Lexington, Kentucky
Image by Richie Wireman

Savor New Flavors

Go international and kick off your visit to Lexington with a full Irish breakfast—complete with grilled tomatoes, baked beans, and black and white pudding—at the Horse & Jockey Pub & Kitchen. Weekend brunch starts at 11 am, and bottomless mimosas and one of the city’s best outdoor patios mean you’ll likely stay a while.

Continue the continental cuisine theme at ItalX downtown, the newest venture by beloved local chef Jonathan Lundy, a former James Beard semifinalist for Best Chef: Southeast. Here, options like housemade cacio e pepe—simple enough to allow the pasta to be the star—and freshly baked focaccia served with whipped ricotta provide a light but filling lunch.

If a midday taco feels more like a fit, stop in at Agave & Rye for a Swipe Right. You’ll get a blend of perfectly seasoned herbed chicken flanked by spicy bacon and aged white cheddar, and you won’t have to pick between crunchy or soft shell, since it comes with both. For dinner, head to the Postmaster’s Pub—housed in a building that was once the oldest-surviving Lexington post office—where the food, as well as the ambiance, are worth writing home about. Snag a grilled-to-perfection sirloin or salmon fillet, or, if carbs are your love language, dive straight into the chef specialty loaded mac and cheese. Don’t worry: Their noodles, topped with smoked gouda mornay, beer-braised pulled pork, honey-lemon barbecue sauce, and, yes, cornbread crumbles, taste just as good as you think they will.

A horse and a foal in the pastures of WinStar in Lexington, Kentucky
Image by Mary Jane Speer

Horse Around in Lexington, Kentucky

In between bites, make time to explore Lexington’s trademark horse scene. It’s easy to spot prize-winning thoroughbreds on a tour at Old Friends Farm in Georgetown, roughly thirty minutes away, where many famed racehorses live out their retired years in bliss. Or, schedule a tour of a working horse farm like Mill Ridge or WinStar through Horse Country, which provides easy online tour booking for dozens of equine operations in the area.

Without even leaving downtown, you can score selfies with dozens of whimsical painted horses dotting the Lexington streets thanks to the once-every-ten-years Horse Mania display, sponsored by the city’s LexArts nonprofit, which happened in 2022. If you happen to be in town in April or October when horse races are held at Keeneland, make it a point to get to the postcard-worthy local racing track—or, circle your calendar for an August track visit when the annual two-day Railbird Festival livens up the grounds with concerts by some of the nation’s best recording artists. 

Diners at Luna in Lexington, Kentucky

Sip and Play in Lexington, Kentucky

After dinner, take the elevator to Infinity Rooftop Restaurant & Bar for drinks atop the city’s newest downtown high-rise, the City Center building on West Main Street. Grab a slice of cheesecake and enjoy a craft cocktail, like the Perch, which complements a dash of Evan Williams bourbon with simple syrup and ginger beer, and take in unbeatable views of the downtown skyline.

If you still have more energy to burn, drop in at LexLive, the city’s new downtown entertainment complex where you can watch the latest movies, challenge your friends to a game of bowling, or enjoy a drink at Corner Bar, which boasts no fewer than fifty premier bourbons and bartenders who know how to use them.Then, to cap off the perfect day, make a nightcap of it at the Grove, a newly created, eclectic downtown hangout that’s home to Luna, a food truck, Fable Charcuterie + Wine, Harvey’s Bar and Beer Garden, and the Melodeon bar and event space. While you’re there sipping a local craft brew, savor the cool vibe of outdoor patio lights and public murals created by buzzworthy Lexington artist Wylie Caudill.

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