This article—shared in partnership with our friends at VisitLex—is part of 52Cities, a column where we share editor-curated and community-loved recommendations for visiting our favorite places.
As a native Atlantan, I’m no stranger to visiting Southern cities—spring breaks spent in Florida beach towns, Girl Scouts trips to Savannah, an especially memorable New Year’s Eve in Nashville, and plenty of weekend getaways in the Carolinas. But up until recently, I’d never spent much time in Kentucky. Sure, there was the family pilgrimage to Mammoth Cave when I was a teenager, too cool to appreciate the wonders of eyeless fish (Google it) and the world’s largest underground cave system, but the Bluegrass State had yet to pull me in. After a recent trip to Lexington, all of that changed.
Now, I’m downright hooked on the magic of that city—its many-patterned jockey silks and early morning race track sounds; its edible flower gardens and bustling farmers’ markets; its rich bourbon history and new-found love of imaginative sake. Lexington is the birthplace of track stars like Secretariat and home to 14 bourbon distilleries, including Fresh Bourbon, one of the “first African American-owned distiller[ies] since slavery.” Its limestone-rich soil is optimal for breeding horses, distilling spirits, and growing all sorts of crops, but most importantly, Lexington’s landscape is ideal for fostering the warm, welcoming community you’ll find there today.
Whether you’re stopping in when the Breeders’ Cup is in town, seeking out the city’s many LGBTQ+ destinations, or simply in search of the perfect weekend trip, Lexington has a little something for everyone.
1. The Manchester Hotel, 941 Manchester St.
Comfy beds, woody accents, clawfoot tubs, and plenty of natural light—what more could you want out of a boutique hotel? Oh, it’s also walking distance from the Distillery District, which is home to breweries, restaurants, and a cidery, plus it’s got two on-site restaurants: Granddam and Lost Palm (more on those later).
2. 21c Museum Hotel Lexington, 167 West Main St.
Contemporary art lovers, this one’s for you. The 21c Museum Hotel boasts incredible city views, a convenient downtown location, and galleries filled with work from local artists. (They’ve also got charming, giant blue penguins to greet you in the lobby.)
3. The Elwood Hotel, 444 Parkway Dr.
Described as “a tribute to contemporary Southern lifestyle,” The Elwood Hotel is just as beautiful on the outside as it is on the inside, thanks to the sprawling floral mural on its facade. It’s got a modern, minimalist aesthetic, an in-house bar and restaurant called Fiddletree Kitchen, and it’s pet-friendly.
4. Pearl’s, 133 North Limestone
By night, Pearl’s is a wood-fired pizza and natural wine bar, but by day they serve wood-fired bagels—plain with cream cheese or as a sandwich featuring eggs from Black Soil KY, an agribusiness whose goal is to reconnect Black Kentuckians with their agricultural heritage—and most importantly, coffee.
5. Josie’s, 821 Chevy Chase Pl.
Take a seat at Josie’s horseshoe-shaped bar and settle in for breakfast, brunch, lunch, or even dinner. We’re talkin’ fluffy waffles, loaded omelets, deli sandwiches, specialty burgers, and wedge salads, all served with a side of Southern comfort.
6. Blue Door Smokehouse, 226 Walton Ave.
You’ll find some of the city’s best barbecue at Blue Door Smokehouse, from tender, smoky brisket to juicy baby back ribs. They’re open Monday through Saturday from 11 a.m. until they sell out, so go early to avoid disappointment.
7. Nourished Folks, 101 W Loudon Ave. Suite 168
Located in Greyline Station, this cozy cafe serves an impressive menu of hearty, from-scratch vegetarian dishes (like their pesto grilled cheese on sourdough), along with plenty of dairy- and gluten-free options.
8. The Social Vegan, 101 W Loudon Ave.
If inventive vegan fare is more your scene, head next door to The Social Vegan (also located in Greyline Station). Their Southern-leaning offerings include cashew cheese dip and chips, buffalo cauliflower wings, and fried oyster mushrooms.
9. North Lime Coffee & Donuts, 101 W Loudon Ave. Suite 160
Choose from their lineup of everyday donuts (Funkfetti, Chocolate Iced, Cinnamon Sugar) or select one of the ever-changing Specialty Donuts du jour. True to form, North Lime has equally creative caffeinated options, like the espresso-filled, peanut buttery, Shaken PB Cup, but no one will judge you if you opt for something simpler.
10. Natalia’s Pastry Shop, 101 W Loudon Ave.
Nestled among the many storefronts in Greyline Station, this Dominican-owned pastry shop has freshly baked goodies ranging from savory empanadas to sweet cupcakes and everything in between.
11. Rise Up Pizza, 101 W Loudon Ave. Suite 112
If you’re lucky enough to find yourself at Rise Up on a Saturday, go ahead and grab a #SaturdaySlice, their perfectly crusty, Sicilian-style slices (I recommend a corner piece). Or, order one of their specialty personal-sized pies any day of the week.
12. Zim’s Cafe, 215 W Main St. Unit 25
Located inside the Old Courthouse, Zim’s is a casual, family-friendly spot from the eight-time James Beard Foundation Award nominee, Chef Outia Michel. Their menu changes based on what’s in season, but it always features a bounty of fresh produce, meat, and more from Kentucky farmers. Psst: Lexington’s Visitor Center is located in the same building, so this is a great place to stop in if you’d like to further immerse yourself in all things LEX.
13. Smithtown Seafood, 501 W 6th St.
Another joint from Outia Michel, Smithtown Seafood is all about—you guessed it—seafood. Enjoy oysters on the half shell, chilled lump crab dip, fried catfish sandwiches, and other locally sourced delights.
14. A Cup of Commonwealth, Multiple Locations
Looking for a cup of Joe to start your day? Stop by one of their locations and fuel up on coffee made from sustainably-grown beans.
15. Holly Hill Inn, 426 N Winter St, Midway, KY
If you can only squeeze one meal from Ouita Michel into your trip, Holly Hill Inn is the spot. Helmed by Culinary Director Tyler McNabb, this pioneering farm-to-table restaurant crafts whimsical prix fixe menus around seasonal, hyperlocal fare in a bucolic setting just outside of Lexington.
16. Lockbox, 167 W Main St.
Dining at Lockbox is a no-brainer if you’re staying at the 21c Museum Hotel (it’s located in the hotel’s lobby), but its downtown location makes it a convenient dinner spot for anyone, guest or not. Order a bunch of bites like their pimento cheese and biscuit-filled share board for the table, or choose a few of their show-stopping mains.
17. Crēaux, 310 W Short St.
Inspired by all things New Orleans, Crēaux is Lexington’s answer to Bourbon Street—that means live music, Hurricanes, and damn good Southern-style fried fish.
18. Granddam, 941 Manchester St.
Named for a retired matriarchal racehorse living her best life as a retiree, The Manchester Hotel’s Granddam is all about taking it easy in style. Sip a tableside julep while you peruse the Appalachian-inspired menu of reimagined Bluegrass fare, sourced primarily from local purveyors.
19. Lost Palm, 941 Manchester St.
If tropical, ‘70s Miami vibes are more your thing, head upstairs at The Manchester Hotel to the Lost Palm rooftop bar. They’ve got seafood towers, shrimp mofongo, and tacos al pastor till 11 p.m., plus plenty of rum-based cocktails, beer, and wine.
20. Proud Mary BBQ, 9079 Old Richmond Rd.
Perched on the Kentucky Riverbank, Proud Mary is known for their killer barbecue, cold drinks, and live music.
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21. Corto Lima, 101 W Short St.
James Beard-nominated chef Jonathan Lundy is behind this downtown, Latin-inspired restaurant. From shrimp ceviche to Peruvian chicken, pretty much everything on the menu pairs well with one of their many signature margaritas.
22. Crank & Boom, Multiple Locations
This craft ice cream parlor has two locations in Lexington, but it’s their Distillery District spot that especially piqued my interest. Enjoying a frosty sweet treat after an afternoon at a brewery? Yes please.
23. Little Fork, 1170 Manchester St. Suite 140
Located at Wise Bird Cider in the Distillery District, this food truck sources ingredients from Black-owned farms through a partnership with Black Soil KY to serve up loaded chicken poppers, fried green tomato burgers, and other cider-friendly fare.
24. Goodfellas Pizzeria, Multiple Locations
With multiple locations around the city—including one in the Distillery District—Goodfellas is a convenient, community-loved pizzeria that’s perfect for grabbing a pie or two.
25. Lussi Brown, 114 Church St.
Pronounced “Lucy” Brown, this all-day coffee shop serves its expertly crafted cocktails from around noon until they close at 10 p.m., Wednesday through Sunday. Take a seat at one of their sidewalk tables and enjoy a Watermelon Mojito, Cold Fashioned, or Earl Grey Mule.
26. Wise Bird Cider Co., 1170 Manchester St. #140
This family-fun operation crafts small-batch ciders using the best Kentucky-grown apples, along with harder-to-find varietals grown in neighboring states like Virginia, Ohio, and Pennsylvania. With seasonal specials like Frosé (aka frozen Rosé Cider) and classics like their semi-dry Commonwealth Gold, you’ve got plenty of options to choose from.
27. Ona’s, 108 Church St.
Open seven days a week from 5 p.m. to 1 a.m., Ona’s is a divey, no-fuss bar that caters to a variety of tastes. Think: $3 High Life, a rotating list of natural wines, and craft cocktails.
28. Darling Wine Bar, 101 W Loudon Ave. Suite 164
This Greyline Station spot is all about natural wine, but they’ve got some cold beer too, if that’s your thing. Formerly The Breeze, Darling Wine Bar is also a bottle shop in case you’re looking to stock your hotel fridge.
29. Crossings, 117 N Limestone
A cornerstone of Lexington’s LGBTQ+ community, Crossings is a queer, downtown dive bar that’s been around for 30 years. Its current owners are committed to creating an inclusive environment for all who enter and describe it as “a home for queers, misfits, and charity.”
30. Talon Winery & Vineyards, 7086 Tates Creek Rd.
Established in 1999 as Fayette County’s first winery, Talon Winery & Vineyards is an ideal place to spend a sunny afternoon tasting wine and soaking up the scenery. Bring a picnic blanket and some snacks to make a full day of it.
31. Mirror Twin Brewing, 725 National Ave.
Named for co-founder Derek DeFranco’s mirror twin (an identical twin with asymmetrical features), this brewery is all about community, good vibes, and great beer. They’re constantly adding new beers to the draught lists in their two side-by-side taprooms—one is fairly standard in design while the other is more of a laid-back lounge.
32. Myriad Meadery, 732 National Ave.
Another brainchild of the Mirror Twin folks, Myriad specializes in all things mead (honey wine). Lead Mazer Doug Price, also a Mirror Twin brewer, is behind their many mead varieties you’ll find on tap, from Blackberry Espresso Session Mead to a Cranberry Hibiscus Mead Spritzer.
33. The Void Sake Company, 949 National Ave. Suite 190
Sake might not be the first thing that comes to mind when you think of Kentucky, but trust me, the folks at The Void know what they’re doing. Visit their sake brewery and try a sake flight, or opt for sake in slushie form if it’s an especially hot day.
34. Ethereal Brewing, 102 W Vine St.
If you’re already in the Distillery District, you might as well mozy on over to Ethereal Brewing, aka the only brewery in town with a dedicated yeast lab. They’ve also got a dog-friendly tap room complete with dart boards and the occasional taco stand.
35. Bourbon on Rye, 115 W Main St.
This Prohibition-style bar and restaurant specializes in elevated cocktails as well as an extensive list of bourbon and rye, naturally. Can’t find something that tickles your fancy on their list? Ask the bartender for the rare bourbon list.
36. Harvey’s Bar, 200 W Main St.
Part of the six-business collective known as The Grove, Harvey’s is a colorful, lively bar with indoor and outdoor seating available. They’ve got beer, wine, and cocktails, and the decor is somewhere between a speakeasy and “Alice in Wonderland.”
37. The Thirsty Fox, 215 W Main St. #50
Inside Zim’s Cafe you’ll find another booze-forward establishment: The Thirsty Fox. Their menu features approachable wines, local beers, unique cocktails, and, of course, bourbon.
38. County Club, 555 Jefferson St.
The sister restaurant of Ona’s, County Club specializes in refreshing cocktails and crushable, natural wine. Their food menu is focused on the art of smoked meats, so it’s worth sticking around for a bite.
39. Keeneland, 4201 Versailles Rd.
Whether you come for a Crafted Event or a good ol’ fashioned horse race, Keeneland is sure to delight. Breakfast at the Track is especially family-friendly, so bring the kiddos along and watch as the jockeys warm up with the horses. They also offer tours of the well-manicured grounds all year long in case breakfast isn’t your thing.
40. Lexington Farmers’ Market, 399 S Broadway
Meet some of those local purveyors IRL at the Lexington Farmers’ Market. The market’s date and location will vary depending on the time of year, so be sure to check their website before you plan to go.
41. Little Sparrow Productions, Multiple Locations
From drag bingo with prizes to emo drag brunch, Little Sparrow Productions puts on spectacular drag shows throughout central and southern Kentucky. Check their Instagram for the latest show schedule, and be sure to bring dollar bills to tip the queens.
42. Mill Ridge Farm, 2800 Bowman Mill Rd.
Horse girls, this one’s for you. The folks at Mill Ridge Farm have been raising and selling racehorses since 1962. Their family-owned farm has bred an impressive number of Derby winners, including Secretariat, Giacomo, Barbaro, and Street Sense. Visitors can tour the farm, but keep in mind that it’s best if you arrive in your own vehicle as there’s some driving required. For best more details on how to visit, check out visithorsecountry.com.
43. Bites of the Bluegrass, Multiple Locations
This walking tour is perfect for those looking to get a feel for the local food scene. In addition to plenty of bites (and cocktails, if you choose that option), your knowledgeable guide will fill you in on Lexington’s history, too.
44. The Legacy Trail, 318 West Loudon Ave.
If it’s not too hot and you’re looking for an outdoor activity, head on over to this shared use greenway trail for a bike, run, or walk through the city. The trail starts at Isaac Murphy Memorial Garden and continues for 12 miles to the Kentucky Horse Park.
45. SoulFeast Week, Multiple Locations
Founded in 2021 by siblings Martina and Marcellus Barksdale, SoulFeast Week is an annual 10-day celebration of Black farmers, chefs, and restaurateurs in central Kentucky. It’s worth planning your entire trip around this week—the festivities include a hip hop brunch, a diaspora dinner, Soulteenth Fest, and more. The dates shift slightly every year, but the week always centers around Juneteenth (the 2023 SoulFeast Week was June 16 through June 25).
46. The Kentucky Castle, 230 Pisgah Pke.
That’s right—Kentucky has its very own castle, and it’s located right outside of Lexington in a town called Versailles (pronounced “ver-SAYLES”). Book a tour of the castle, farm, or both, then enjoy a meal at the on-site restaurant.
47. Fresh Bourbon Distillery 377 E Main St.
Experience a full sensory bourbon tasting at the Fresh Bourbon Distillery. You’ll need to buy tickets in advance via their website, so plan accordingly.
48. Vintage Therapy, 101 W Loudon Ave. Suite 178
Pop into Vintage Therapy once you’ve had your fill of snacks at Greyline Station and prepare to be delighted by the sheer volume of well-curated vintage clothes and assorted ‘90s ephemera. Bonus: They offer free shipping, so you can shop their shelves even when you’re back home.
49. The Domestic, 945 National Ave.
The Domestic is a classic booth-style antique and vintage shop with assorted vendors throughout. Browse for art, pottery, home goods, books, clothing, accessories, furniture, and more—and be sure to say hi to the shop cat.
50. Wearhouse, 941 National Ave. #120
This vintage boutique specializes in high-end clothing, accessories, furniture, and art. Owners Shanda and Liz are sustainability advocates and vintage enthusiasts, so you’ll be in good hands when you step into their shop.
51. Forage, 803 N Limestone Suite 170
Consider this your one-stop shop for plants, flowers, and sustainable living. Forage is home to Lexington’s first refillery, a place where you can refill bottles of all-purpose cleaner, toothpaste, shampoo, and more.
52. Creatures of Whim, 126 N Broadway
At Creatures of Whim, you’ll find a curated assortment of handmade goods such as clothing, accessories, and candles. You’ll also find tarot cards, crystals, sage, and ritual tools.