Each year, the first Saturday of May shines a spotlight on Louisville, Kentucky, when thousands of well-heeled people arrive for the Kentucky Derby. Ostensibly, it’s a chance to cheer on the fastest three-year-old thoroughbred horses in their 1.25-mile-long race at Churchill Downs—but the festivities start well before Derby day. Insiders know to arrive in time for the Kentucky Oaks, the fillies race the Friday before, and not to miss the “walk out,” when the 20 star thoroughbreds walk from the barn to the paddock at Churchill Downs before getting saddled up for the Derby. Here’s our guide to keeping the bourbon and mint juleps flowing and experiencing the best Louisville has to offer. 

Where to stay in Louisville

Hotel Bourré Bonne, one of Louisville’s newest luxury properties, marries French elegance with Kentucky heritage. Its name—French for “good bet”—is both a nod to horse racing and a hospitality promise. A rooftop lounge and pool set the social tone, while Steakhouse Bourré Bonne ups the ante with a signature bourbon bar, tableside martini service, an Hermés-themed private booth, and a curated gallery wall (look out for a Picasso). Come Derby weekend, the hotel leans into its glam: guests can book in-room hair and makeup services, shop at a pop-up for statement hats and fascinators, and stop by the lobby for a Four Roses bourbon event. 

21C Museum Hotel Louisville is equal parts contemporary art museum and boutique hotel. It bills itself as the world’s first museum hotel with free galleries open 24/7 so guests can stop by at their leisure. In the lead-up to the Derby, the “pink snail migration” pops up overnight—look out for 35 oversized neon sculptures making their way (slowly) from Goshen to downtown Louisville in the name of charity. 

The Seelbach Hilton has defined grandeur in Louisville since its opening in 1905. It is pure Beaux-Arts splendor steeped in literary lore. F. Scott Fitzgerald, who was stationed nearby during WWI, frequently visited (and was occasionally kicked out of) the Rathskeller Bar. He created a heroine from Louisville in The Great Gatsby, and the hotel’s grand ballroom famously inspired Tom and Daisy’s wedding location. Today, the Gatsby Suite and a menu of Prohibition-era cocktails keep that connection alive. The Steelback Suite—largely unchanged since its debut—has hosted presidents, rock royalty, and Hollywood stars, including Harry Truman, Keith Richards, and Linda Gray. Even the scandals are tinged with cinematic drama. On Derby Day in 1923, four masked bandits raided the hotel poker room, escaping into the crowds with what would now amount to a small fortune.

Where to eat and drink around the Kentucky Derby

Louisville’s fine-dining scene leans meat forward and Southern, though Edward Lee’s 610 Magnolia is a cut above the rest. Since 2003 the chef-owner has sparked joy with his modern approach to Southern cooking—a tasting menu that incorporates local traditions and diverse food cultures (his Korean heritage among them). The wine, bourbon, and cocktail menus are equally thoughtful. Meanwhile, Proof on Main is an artsy dining destination known for its farm-to-table ethos that showcases elevated Southern and Appalachian-inspired food alongside one of the city’s most compelling bourbon programs. Swizzle Dinner & Drinks delivers retro glam atop the Galt House with two revolving floors unveiling ever-changing skyline views. A dedicated Derby menu and an open-concept kitchen create a fun, kitschy-yet-upscale experience. 

When it comes to high-energy, see-and-be-seen scenes, Louisville’s steakhouses are the hotspots during Derby weekend. Jeff Ruby’s Steakhouse is an unapologetically old school, white-tablecloth spot where the energy soars during Derby weekend. The award-winning steakhouse and seafood spot leans into the vibe: all glittering chandeliers, red velvet banquettes, and red and gold carpets. Repeal Oak Fired Steakhouse is a trendy restaurant on Whiskey Row, where oak-fired meats and seafood come alongside one of the city’s largest bourbon collections (including the restaurant’s exclusive private barrels). The setting—a former J.T.S. Brown & Son distillery—draws a crowd throughout Derby weekend.

For a Louisville institution with deep Kentucky Derby ties, look no further than Jack Fry’s iconic dining room. In 1933, Jack and his wife Flossie opened the restaurant—but Jack’s penchant for gambling, horse racing, boxing, and occasional bootlegging out of the back room put the establishment on the map. A 1985 transformation turned Jack Fry’s into one of the city’s definitive fine dining spots. Today, the restaurant serves a contemporary American menu with subtle Southern flair. 

Speakeasies round out a spirited evening—most notably Hell or High Water, a cozy hideout beneath Whiskey Row where craft cocktails and an extensive bourbon list set the tone for late-night revelry.

VIP experiences 

Three icons define the Kentucky Derby worldwide: the mint julep, elite thoroughbred horses, and outrageous chic hats. Woodford Reserve raises the bar on the mint julep this time of year with $2,000 and $5,000 versions in specialty hand-crafted cups. Just 152 cups are produced, each adorned with a sculpted thoroughbred encircled by 13 stars, designed by Graham Newton of From the Vault. For a true behind-the-scenes look into horse racing and raising, Mint Julep Tours pairs a thoroughbred farm visit (complete with racing legends) with a distillery tour and tasting (at either Buffalo Trace or Bulleit). Derby season is also a rare chance to appreciate the art of custom millinery. At Atelier Formé Millinery, guests can commission or purchase custom handmade hats alongside master milliner Jenny Pfanenstiel, who helps everyone look their Derby best. 

There’s no limit to the VIP experiences, spanning private suites, behind-the-scenes access, and bespoke bourbon experiences along the Bourbon Trail. At Clayton & Crume, the annual Oaks Day Brunch unfolds as a four-course menu by Wiltshire Pantry, paired with Maker’s Mark cocktails served at a communal table inside Muhammad Ali’s former boxing gym. Guests at Angel’s Envy can select and buy a custom barrel, sample newly released cask-strength bourbons, or bottle their own 115-proof Angel’s Envy Single Barrel.