You can thank Bonnaroo, that annual extravaganza of music and flower crowns, for transforming Nashville’s image—from cowboy enclave to hipster haven—within a certain segment of trend-watching travelers. But by now, Nashville is starting to go the way of your once-favorite indie band after its big breakthrough; certain discoveries lose their luster once everyone is listening.

Think of its smaller northern neighbor, Louisville, Kentucky, as the up-and-coming act that’s about to break through. From a prospective visitor’s perspective, the riverside city is probably most associated with May’s annual Kentucky Derby—but there’s much more than horse racing and mint juleps to lure travelers. In particular, Louisville’s restaurant and bar culture is galloping ahead at full speed. And it’s cultivating a cool, youthful energy that still feels largely undiscovered by the masses.

Louisville is a city of scattered neighborhoods, and unsurprisingly, downtown is probably the best-situated spot from which to explore. So hang your hat at the stylish and modern 21c Museum Hotel, a 90-room boutique property that does double duty as a fully curated art gallery with rotating exhibitions. There’s a sense of whimsy and irreverence, from the human-sized statues of red penguins—the museum’s mascots—that pop up in unexpected locations (like your guest room) to the lobby’s massive sculpture of silver-painted household junk swept up into a funnel-like vortex. (It’s inspired by a tornado that devastated Louisville in the ’70s.) For the coolest accommodations, check into the Cyclone, an art installation-slash-sequestered guest room. Outfitted with a vinyl record collection and a cabinet of quirky curios, this hermetic hipster den is swathed in barn wood and boasts a domed ceiling of colorful crazy-quilt patchwork panels. It’s like sleeping in Juno’s womb.

The hotel is also home to the buzzy Proof on Main, awarded Best American Hotel Bar at last year’s Tales of the Cocktail (aka the Oscars of booze). But Proof’s wonderful whiskey-centric cocktails, buttressed by some inventive and upscale spins on Southern cuisine, represent just a small sip of what you’ll find in Louisville’s bar scene. Stumble your way through the Urban Bourbon Trail, a list of about 30 bars that all have at least 50 varieties of the Bluegrass State’s signature spirit. They’re wildly different, ranging from Haymarket Whiskey Bar, a kitschy bric-a-brac-strewn dive where artsy Gen-Y crowds pound shots over pinball and shuffle feet to live bands, to the Seelbach Hotel, a historic Gilded Age holdover that helped inspire Fitzgerald’s The Great Gatsby. (Scenes from the 2013 movie were shot here.) And some of these bourbon joints are just as strong on the culinary side. For old-school class and a comfort-food classics, hit the grand Brown Hotel, birthplace of the Hot Brown: a skillet-served open-faced sandwich of turkey, bacon, tomato and Mornay sauce, now a Southern cuisine staple, that’s worth every calorific bite. And on the nouveau gastropub front, fly to Doc Crow’s, a “Southern smokehouse and raw bar” where the massive whiskey list washes down baby back ribs, shrimp and cheddar grits, and cornmeal-crusted oysters with a spicy remoulade.

Some of Louisville’s most exciting new food-and-drink destinations wait in the ’hoods surrounding downtown. Neighboring NuLu (“New Louisville”) is where the flannel- and bootie-clad hep cats strut among art galleries, vintage clothing and record shops (like Bermuda Highway, owned by Houndmouth frontwoman Katie Toupin), and playful bars and restaurants. Take Garage Bar, a former gas station rehabbed as a craft beer and artisanal pizza hangout, where outdoor pingpong tables glow in the dark come dusk, or Decca, with its upstairs New American dining room and subterranean cellar lounge, where tipplers soak up vintage jukebox jams and reels of black-and-white movies projected against the cool stone walls.

Stroll even farther out to find Butchertown, a neighborhood that is home to two-year-old Copper & Kings, Kentucky’s first exclusive brandy distillery, one with a rock ’n’ roll spirit. Its copper stills are named after Bob Dylan songs, and the brandy is matured in wooden barrels that are assailed 24/7 with sound waves from booming subwoofers. (The team even themes its playlists: Prepping for a Boston launch, the Copper & Kings crew blasted barrels with Aerosmith and other hometown heroes.) And it’s home to Butchertown Grocery, the city’s darling new bistro, where chef Bobby Benjamin, a Rhode Island native, turns out a snazzy but unpretentious splay of European-inspired American eats: Think 55-day dry-aged rib-eye with truffle béarnaise and pork belly served with sundried tomato pesto. It’s the flagship foodie draw in a gritty district that, like Louisville at large, is poised to explode. Listen up.

Traveler’s Checks

-Beer snobs: Hit the Highlands neighborhood’s Holy Grale, a suds-soaked gastropub housed in a 1905 church, and fill a growler at just-opened Germantown brewpub Monnik Beer Co.

-Need a food and booze break? Check out Louisville Mega Cavern, billed as the world’s only fully underground zip line course, or take a day trip to Mammoth Cave National Park, the world’s longest known cave system, located a 90-minute drive south.

-History buffs should take a walking tour through Old Louisville, which rivals the South End as one of America’s largest preserved districts of Victorian architecture.

21c Museum Hotel, 21cmuseumhotels.com; Bermuda Highway, 502-553-4576; The Brown Hotel, brownhotel.com; Butchertown Grocery, butchertowngrocery.com; Copper & Kings, copperandkings.com; Decca, deccarestaurant.com; Doc Crow’s, doccrows.com; Garage Bar, garageonmarket.com; Haymarket Whiskey Bar, 502-442-0523; Holy Grale, holygralelouisville.com; Louisville Mega Cavern, louisvillemegacavern.com; Mammoth Cave National Park, nps.gov/maca; Monnik Beer Co., 502-742-6564; Proof on Main, proofonmain.com; Seelbach Hotel, seelbachhilton.com