Road Trip: Louisville, KY

Walkable and culturally rich, Derby City should be a must-see stop on your next road trip

The Big Four Bridge over the Ohio River
Photo by Jacob Zimmer

Miles from Palm Beach: 1,019

This diverse city of more than 600,000 accents its scenic locale on the Ohio River with one-of-a-kind activities that speak to its distinctly Southern heritage. In addition to such marquee attractions as the Kentucky Center for the Performing Arts and the Muhammad Ali Center, Louisville is also home to the Kentucky Derby at Churchill Downs. One of the best ways to spend the day in Derby City is to explore it by foot, traversing its myriad preservation districts and parks, 17 of which were designed by Frederick Law Olmsted. For a panoramic view of Louisville’s skyline and architecture—a blend of old and new that pairs Victorian homes and cast-iron structures with downtown skyscrapers—hop onto the Belle of Louisville, the oldest Mississippi-style steamboat still in operation.

The Muhammad Ali Suite at The Brown Hotel


Part of Louisville’s charm is due to its mix of bygone brilliance and modern energy, a marriage on full display in the ornate lobby of The Brown Hotel. Upon opening in 1923, the elegant Georgian Revival building, now listed on the National Register of Historic Places, quickly became the city’s business and social center. Today travelers and locals gather at the downtown hotel for spirited conversation, drinks, and light dining at the English Grill. For a nightcap, sample one of more than 140 choices of rare bourbon, The Brown’s tribute to Louisville’s favorite sip. When it comes time to sleep, go for the greatest and stay in the Muhammad Ali Suite, decked out in photographs of the hometown hero and memorabilia from his years as a boxer and humanitarian. 

Fourth Street Live

See + Do

While downtown, visit the Louisville Slugger Museum & Factory to learn about the history of the baseball bat and other facts. Afterward make your way down Museum Row and tour the Kentucky Museum of Arts & Crafts to connect with the creative world. Downtown Louisville is also an epicenter for entertainment, and there are a number of live music venues just a short stroll from The Brown Hotel, including the Mercury Ballroom, the Palace Theatre, and nightlife hub Fourth Street Live.


Don’t leave The Brown without indulging in The Hot Brown, a culinary legend that dates back to 1926, when one of the hotel’s chefs crafted an upscale take on hangover food. His open-faced turkey sandwich, traditionally served with bacon, tomatoes, and a Mornay sauce, has since become synonymous with Kentucky cuisine.

Proof on Main
Photo by GLINTstudios

Foodies with a passion for art should visit Proof on Main in 21c Louisville, a hotel-meets-museum concept that presents rotating and permanent contemporary art exhibitions. Amid canvas-covered brick walls and bay windows facing the busy street, chef Jonathan Searle prepares a straightforward, seasonal menu inspired by local ingredients, including a weekly Derby City lunch special that’s updated every Monday. Save room for dessert (homemade lemon gelato, anyone?) as well as the cotton candy that comes with every check.

The Hot Brown at The Brown Hotel
Photo by Chris Witzke

Another great dining option is Decca located in the middle of the up-and-coming NuLu district. Here, James Beard–nominated chef Annie Pettry combines fresh flavors from the South with the Appalachian delicacies of her childhood. Sit upstairs in the vintage record and book shop that doubles as a private dining room, or head downstairs to The Cellar Lounge for music, bar bites, and divine craft cocktails.

Don’t miss: No trip to the Bluegrass State is complete without bourbon. Begin the Louisville leg of your adventure on the Kentucky Bourbon Trail by picking up a passport at the welcome center at the Frazier History Museum. About 95 percent of the world’s bourbon is distilled and aged in Kentucky, and Louisville boasts no fewer than 10 distilleries that offer an in-depth look at the art and science of crafting this Southern spirit.


For unique culinary and retail finds, visit Butchertown Market and tree-lined Frankfort Avenue. There’s also The Highlands, an area between Baxter Avenue and Bardstown Road long known as Restaurant Row that’s packed with unusual retail, bistros, and bars.

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