Cactus Tacos, Drag Shows, and Legendary Blues: Why Lexington, KY, Should Be Your Next Long Weekend

Lexington is home to more than 100 independently owned non-chain restaurants serving everything from traditional Southern fare, to authentic global cuisine, to the aforementioned fresh seafood — an anomaly made possible by the city’s proximity to UPS’s international hub in Louisville, where fish arrives from all over the world within hours of being caught.

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At Tortilleria y Taqueria Ramirez, two generations of the Ramírez family have been dishing out genuine Guadalajaran flavors since 1996. In addition to the usual chicken and beef options, diners can fill their freshly made roasted corn tortillas with lengua (tongue), tripa (intestine), and chicharron (pork rind). This vegetarian went with nopales — a cactus with a mild flavor and pleasing texture that I hope to see on more Mexican menus near me.

There are nearly 20 Latinx-owned and/or -led eateries in Lexington, a result of this population’s strong ties to the area’s horse industry. Other immigrant influences have resulted in restaurants specializing in Greek, Vietnamese, Italian, French, Korean, and, thanks in large part to UPS, sushi.

Lexington native Chef Ouita Michel, a six-time James Beard Foundation (JBF) nominee, just launched her ninth restaurant located in and around her hometown. From fine dining at the Holly Hill Inn — where you can find elegant French twists on comfort classics like shepard’s pie vol au vent (filled puff pastry) and apple tarte tatin (upside-down tart) — to po-boys and burgers at the casual Windy Corner Market, Michel prioritizes the use of locally grown ingredients sourced straight from nearby family farms. I had lunch at Windy Corner, filling my belly with crispy parmesan-bound artichoke fritters dipped in a tangy homemade remoulade and a superfood salad whose addition of toasted pumpkin seeds and lightly fried tofu made for a delightful range of textures.

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To say I ate well in Lexington would be a gross understatement. There was the broccolini bagna cauda (garlic, anchovies, and olive oil dipping sauce) and gnocchi in brown butter cream sauce at Eppings on Eastside; the Korean fried cauliflower and wilted Brussels sprout salad at Dudley’s on Short; and the mushroom bolón (Ecuadorian mashed plantain fritter) and vegetable ceviche at Lost Palm — a tropical rooftop oasis helmed by Chef Paula Endara, another JBF-recognized chef and contestant on Bravo’s Top Chef Season 22.

My apologies to the carnivores out there; you’ll just have to visit yourself to experience Lexington’s variety of meat dishes, like the traditional Hot Brown sandwich (an open-faced sandwich with turkey, bacon, and cheesy mornay sauce), hearty Burgoo stew (made with a combination of meats and vegetables), smoky barbecue, and, of course, fried chicken.

Locals like to say that Lexington is a blue city in a red state, thanks to its long history of progressive action. In 1999, Fayette County was the first in Kentucky to pass a county-wide Fairness Ordinance that protects residents from any type of discrimination based on sexual orientation or gender identity. Lexington elected the state’s first openly gay mayor, Jim Gray, in 2010. City employees have had access to domestic partner benefits since 2013, and there’s been a ban on conversion therapy for LGBTQ+ youth since 2021. In 2024, Lexington ranked 13th in the nation on the Human Rights Campaign Municipal Equality Index, which evaluates the LGBTQ+ policies, laws, and services of more than 500 American cities.

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You can’t walk around downtown without spotting pride flags on nearly every corner — flying from poles, posted in shop windows, and painted on crosswalks. And while everyone is welcome everywhere, there are a few places of particular importance that anyone interested in queer culture should check out.

The Bar Complex is a nighttime hotspot featuring three separate spaces for drinking, dancing, and catching a monthly art exhibit or a nightly drag show. It’s housed on the site of the former Gilded Cage, a gay nightclub opened in 1963 — predating the 1969 uprising at New York’s famous Stonewall Inn. It’s also the site of the 1970 wedding of Marjorie Jones and Tracy Knight, the first lesbian couple in the US to sue for a marriage license.

For a chiller vibe, head to Lussi Brown Coffee Bar, which has become a staple of Lexington’s LGBTQ+ community not just for its exceptional coffee and innovative cocktails, but also for its commitment to providing a safe, welcoming space where everyone is free to be themselves. Just down the street, the “Mother of Us All” wall mural pays homage to Sweet Evening Breeze, a gay Black drag queen who began hosting public drag performances in Lexington in the 1920s. Yes, you read that right — the 1920s.

For more on Lexington’s LGBTQ+ scene — including events, activities, and ways to get involved — the Lexington Pride Center is a fantastic resource for locals and visitors alike.

Photo: Allison Savage Bates

While Kentucky is the birthplace of bluegrass and has produced country music stars like Chris Stapleton and The Judds, it’s also the only place in the world where you can catch a live performance from the legendary blues artist Tee Dee Young.

Born in Lexington in 1954, Tee Dee was playing to sold-out arenas by age 13 and has opened for and played with the likes of The Jackson Five, Aretha Franklin, James Brown, and many more. Although he’s performed all over the world, these days, there’s just one place you can find him: his namesake lounge in his hometown — an unassuming hole-in-the-wall that’s only open on Monday nights and only accepts cash.

Entering the dark, cramped room feels a little like walking in on a wedding or family reunion: Auntie So-and-So takes your cash and gives you your ticket; Cousin What’s-His-Name delivers your drink order; and there, on the flat, floor-level stage just a few feet from where you sit, Uncle Tee Dee and his band jam long into the night. It’s impossible not to get swept up in the emotion emanating from Tee Dee’s guitar and the pure joy that spreads across his face as he plays, whether it’s a mournful blues riff or a toe-tapping party beat that gets everyone out of their seats.

If anything’s worth staying out late on a school night for, it’s definitely Tee Dee’s Lounge.

Photos: Allison Savage Bates

As I mentioned in the beginning, Lexington is known primarily for horses and bourbon. And the reason why can be traced back to prehistoric times.

Underneath the city lies a large bed of limestone — sedimentary rock composed primarily of calcium carbonate — a remnant of the shallow tropical sea that covered much of Kentucky around 450 million years ago. The limestone imparts calcium and other minerals into the soil to produce nutrient-rich grass, which in turn helps cultivate strong bones and powerful muscles in the horses that eat it.

Lexington is widely regarded as “The Horse Capital of the World.” The area has more than 450 horse farms that produce the finest thoroughbred racing horses ever to grace the track, including Secretariat, Sea Biscuit, and Lexington, the revered champion named after the city where he was born, raised, and raced. Fun fact: Horse-racing fan Queen Elizabeth II was a frequent visitor to Lexington, reportedly declaring it her favorite place in the US.

Additionally, the limestone acts as a natural water purifier, filtering out iron to produce sweet-tasting mineral water. And because bourbon can be as much as 60 percent water, it’s a major factor in the quality and flavor of the final product. Water continues to play a role throughout the aging, batching, and bottling processes, not to mention the growing of the corn that must, by definition, comprise at least 51 percent of the grain mixture used to create bourbon.

There’s no shortage of places in Lexington to learn more about the city’s legacy of both horse and bourbon culture. Visit a horse farm for a peek behind the breeding curtain, spend a day watching the races at Keeneland, tour one of the 18 local and regional distilleries, or sidle up to just about any bar for a master class in bourbon tasting.

Even the airport bar has a bourbon list that requires a legend and a server who knows more about the stuff than I’ll ever be able to fully appreciate.

Photos: Allison Savage Bates

• Where to stay: The 21c Museum Hotel in downtown Lexington is a comfortable, conveniently located basecamp that doubles as a funky art gallery.
• How to get there: Lexington is located within a day’s drive of two-thirds of the US. Alternatively, nonstop flights into Blue Grass Airport depart daily from 18 cities as far away as Las Vegas, New York, and Fort Lauderdale.
• How to plan your trip: Need help putting together your Lexington itinerary? Let a horse plan your experience through Neigh-I, “the world’s first horse-powered travel planner.” Seriously. I did, and I had an amazing adventure.