1792 City Guides: Lexington, Kentucky

by Scott Wagner

What to do, where to sleep, and where to eat in the heart of the Bluegrass

When it comes time to chart your summer getaways, consider putting Lexington, Kentucky, on your map. About half the size of Louisville—the state’s other, better-known city where the Derby takes place—it’s got the charm of a southern town with plenty to keep you occupied during a few days away. Once called the Athens of the West, we’d argue that the name still rings true: thoroughbreds, bourbon, farm-to-table food, and a burgeoning art scene make for a unique, happening, low-key, and hip place. Below, check out a few of our recs for where to go and what to see. 

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Where to Stay 

21c Hotel 

Part art gallery, part boutique hotel, 21c is the place to stay if you’re into design. Housed in what was once a grand old bank, contemporary interiors by Deborah Berke Partners were merged stylishly with original architectural details like coffered ceilings, terrazzo floors, and a classic limestone facade. Fan of The Queen’s Gambit? Book a night in the Harmon Room, which features mid century furniture, chess-themed wallpaper, and a guide to area landmarks you’ll recognize from the show. 

Where to Eat 


Pizza. Oysters. Good bourbon. If you’re into any of these things, Pearl’s has got you covered. The place prides itself on inventive twists to the Neapolitan pie and does not disappoint. There’s the Euro ‘72 with chili cream and charred broccoli, the Hellbabe featuring quality parm and hot honey, and everyone’s secret favorite side of ranch to boot. There’s also no shame in sharing a dozen oysters on the half shell with a Wildflower bourbon cocktail to start. 

Dudley’s on Short

The kind of place where the judge has a table, Dudley’s is an award-winning spot and longtime local favorite. Run by Lexingtonian Debbie Long for forty years and counting, it serves up Southern cuisine in an upscale setting that’s got “date night” written all over it. Book in advance, if you’re so inclined, and ask for a table on the rooftop for some stellar atmosphere in the heart of downtown. 

Kentucky Native Cafe

Stop at the Kentucky Native Cafe for an afternoon pick-me-up or if you’re looking for a spot where you can eat outside. Designed like a beer garden, tables and chairs are arranged under a canopy of trees where people (and their dogs) come to hang without airs. 

What to Do 


Keeneland is what Lexingtonians mean when they say “off to the races.” Seriously. It’s where the country’s best thoroughbreds run in spring and fall, but even if you miss said meets, the landscaped grounds and historic track can be experienced by way of a walking tour. 

Institute 193

A one room gallery space, Institute 193 is where groundbreaking works by some of the region’s best contemporary artists are shown. And although it may be small, rest assured that whatever’s on view will most definitely not disappoint. 

Shop Local, Shop Vintage 


A hidden gem packed with ever changing displays of vintage furniture ranging from traditional to mid century, Scout is the store to visit if your weekend getaway involves a truck or willingness to ship. Big city goods without the big city prices, as they say, and it’s run by people who will always take the time to help you find what you need. 

The Domestic 

At The Domestic, you’ll find vintage home goods in front and an impressive load of vintage clothes in back. Just prepare to spend some time—it’s a warehouse of vendor run booths you could easily spend a few hours picking through. In need of a Stetson? They probably have it. A belt buckle? Yep, and a bolo to match. Basketball tees? Look no further. 

For more about Lexington, pay a visit to VisitLex, which has much more about the area, attractions and great bourbon.

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