Off to the Races

America’s oldest continually held major sporting event is run every year on the first Saturday in May. Like the onset of spring itself, the Kentucky Derby is a colorful cacophony of sight, sound and smell.

Visitors—decked out in fine suits, flowered dresses and all manner of memorable hats—sip on mint juleps and cheer as three-year-old thoroughbreds tear up the 10-furlong (1.25 mile/ 2 km) oval track at Louisville, Kentucky’s historic Churchill Downs Racetrack.

The 152nd running of the Kentucky Derby, presented by Woodford Reserve, takes place Saturday, May 2, 2026 but preparations get underway long before that. Horses from the U.S. and around the world earn points by winning qualifying races through the Road to the Kentucky Derby. The top 20 will advance to Louisville, where they will line up behind a special starting gate that is only used once a year.

Louisville itself is bustling two weeks prior to the race, with fireworks shows, celebrity parties and the renowned Taste of Derby culinary experiences. The day prior to the Derby is always reserved for the running of the Longines Kentucky Oaks, America’s premier race for three-year-old fillies, where the winning horse is presented with the traditional “Lilies for the Fillies” garland.

The next day is all about the roses, as thousands of people flock to Churchill Downs for the headline event: the Kentucky Derby. The “Run for the Roses®” culminates with the victor’s trot to the horseshoe-shaped Winner’s Circle where they are draped in the traditional blanket of red roses—the official event flower since the 1890s.

“I really think that no other sporting event is as alluring, as captivating, as the Derby,” said Sarah Contardo, Senior Vice President of Sales & Strategy for the Kentucky Derby and Churchill Downs Racetrack.

“Part of it is this mystique that’s hard to describe unless you’ve been there. When you’re betting on a horse, you’re buying into it. There is nothing like it. The entire day, the pageantry, is a spectacle in and of itself.”

Contardo’s team specializes in crafting Derby experiences, including premium hospitality packages with a uniquely Kentucky flair.

Entering Churchill Downs, where history greets you.

“The Woodford Reserve Paddock Club & Enclosure is one of the most popular,” she said.

Featuring rare paddock access and railside race viewing, combined with luxury food and beverage service, a private betting parlor and dedicated concierge service, the Paddock Club is an unforgettable race experience.

Paddock Club dining, a highly sought-after experience.

“You can feel the pounding in your chest as the horses go by,” continued Contardo. “And, of course, you have access to the paddock itself, which is traditionally only allowed for working horsemen.”

Derby days can be further personalized with bourbon and wine tastings, including rare vintages that are hard to find outside Kentucky.

First-time visitors to the Derby may wonder what to wear, and Contardo offered this advice: “Everyone is dressed to the nines. Some are in southern florals and patterns with big hats, while others are more refined in designer clothing that is simpler and more elegant. The style reflects the person. But there remains a sense of the spring garden party—so there is a lot of florals and pastels.”

Bold hats, beautiful dresses, and timeless Kentucky Derby style.

Topping off this finery are traditional Derby headgear options, including full-brimmed hats or statement-making fascinators, which are smaller headpieces attached to a band or clip. For the men, it’s dapper Panama hats, fedoras and bowlers.

As for footwear, Contardo recommends something comfortable for the outdoor sporting event, noting that rough cobblestones can make wedges a safer choice for ladies than high heels.

“The Derby is really a full-blown cultural event steeped in pageantry, fashion and tradition,” she continued. “There are the fashion hats, traditional food and our official beverage, the (bourbon-based) mint julep. There is the singing of ‘My Old Kentucky Home’ just prior to the race. You have the call to the post, the winner, the garland of roses. And at the very core of who we are is our building, with the Twin Spires built in 1895.”

The classic mint julep - crisp, cool, and perfectly at home trackside.

Contardo’s team stands ready to help guests tailor their visit to Kentucky, with recommendations for unique accommodations, local bourbon distillery tours, horse farm tours and more.

“Depending on how adventurous people are feeling, we also have Mammoth Cave National Park, 1.5 hours south of us. In Louisville itself we have the Louisville Slugger Museum & Factory, the Muhammad Ali Center museum, the Louisville Bats Minor League Baseball team and Louisville City FC soccer."

“It’s wise to plan your Derby visit early,” concluded Contardo. “Just reach out to us and we will curate a package for you.”

From the thunder of hooves at Churchill Downs to Louisville’s southern charm, the Kentucky Derby is more than a race—it’s a timeless celebration of sport, style and tradition. Each May, the “Run for the Roses” captivates the world, creating unforgettable moments that endure long after the final stretch. ✈