The Kentucky Derby, often called “The Most Exciting Two Minutes in Sports,” is the longest-running horse race in the United States. It first took place in 1875 at Churchill Downs in Louisville, Kentucky, inspired by European horse races like the Epsom Derby in England and the Grand Prix de Paris. Over the years, it has become one of the most prestigious horse races in the world, marking the first leg of the Triple Crown (followed by the Preakness Stakes and Belmont Stakes).

If you’re visiting Louisville, Kentucky, for Derby Week, you’re in for one of the most thrilling and luxurious experiences in American sports. The Kentucky Derby isn’t just a single race on the first Saturday in May —it’s a week-long festival of events, fashion, bourbon, cigars, and world-class horse racing. Here’s what you can expect if you're traveling to experience the Kentucky Derby

Kentucky Derby Week Racing Events & Schedule

Kentucky Derby Week is packed with high-stakes horse racing, culminating in the Kentucky Derby on the first Saturday of May. Here’s how the week unfolds:

• Opening Night (Saturday before Derby Week): A lively evening of racing under the lights, with music and cocktails.
• Dawn at the Downs (Sunday–Thursday): Watch morning workouts as Derby contenders train at sunrise. Free to attend!
• 502'sDay (Tuesday): Celebrates the community, Louisville's Kentucky Derby tradition makers, inspiration providers and die-hard Derby fans.
• Winsday (Wednesday): New for 2025 Winsday debuts as a day to shine the spotlight on Louisville’s robust nonprofit community.
• Thurby (Thursday): A local favorite featuring great racing, bourbon, and cigars without the full Derby-day madness. 
• Kentucky Oaks (Friday): The biggest race for fillies (female horses). A more elegant, pink-themed event supporting breast cancer awareness.
• Kentucky Derby (Saturday): The main event! The Run for the Roses lasts just two minutes, but the celebration lasts all day.

The Cigar Culture at the Derby: A Winning Tradition

Around the grounds of Churchill Downs, you'll notice a heavily integrated presence of cigars. Horse racing and cigars have been deeply tied to the Kentucky Derby for over a century, evolving into a symbol of celebration, luxury, and victory. Here’s how they became a Derby tradition:

The Culture of Celebration

From the beginning, the Kentucky Derby attracted high society, politicians, and wealthy businessmen, who were known for smoking fine cigars at exclusive gatherings. Winning big at the Derby has always been cause for celebration, and nothing says success quite like lighting up a high-end cigar.

Owners, Trainers & Jockeys

Many horse owners, trainers, and even jockeys have been cigar aficionados. It’s common to see owners enjoying cigars while watching their horses race, and many winners have been known to light up after a big victory.

The Celebrity Factor

Over the decades, Hollywood stars, athletes, and musicians have flocked to Churchill Downs for the Derby. Many of them—like Frank Sinatra, Michael Jordan, and Arnold Schwarzenegger—are famous cigar lovers. Their presence helped cement cigars as a staple of Derby luxury.

Cigar Lounges & VIP Experiences

Churchill Downs has hosted cigar lounges and VIP smoking areas for high-end guests, where premium brands offer limited-edition cigars crafted just for Derby weekend. These exclusive experiences reinforce cigars as a part of Derby culture.

Bourbon & Cigars: The Perfect Pairing

Kentucky is famous for its bourbon, and the Derby is one of the biggest bourbon-drinking events in the world. Since bourbon and cigars pair exceptionally well, it’s natural that cigar smoking became an integral part of Derby festivities.

Modern-Day Derby Cigar Culture

Today, the tradition continues stronger than ever. Whether you’re a racehorse owner, a high-stakes gambler, or just a fan soaking in the Derby atmosphere, a good cigar is often part of the experience. Major cigar brands frequently release Derby-themed cigars, and some lounges in Louisville even host special cigar events during Derby weekend.

The Kentucky Derby isn’t just about horses—it’s about history, elegance, and tradition. And in that tradition, cigars have found a home as the ultimate symbol of celebration.

Experience Cigars During Derby Week

Cigars are deeply tied to Derby luxury. Expect to see owners, celebrities, and VIPs lighting up premium cigars while sipping bourbon. Here’s how you can enjoy cigars during Derby Week:

• Buy cigars inside Churchill Downs at any of the Liquor Barn Tents. Word of caution, you can buy the cigar but if you don't want to light it up immediately you will need your own cigar cutter and cigar lighter.
• VIP Cigar Lounges: Exclusive areas where you can smoke premium cigars with high-end seating and bourbon pairings.
• As April 2025 Louisville will allow smoking cigars indoors at cigar bars. Many top cigar lounges in town host Derby-themed events. 
• Bring Your Own Cigar: If you’re attending the Derby, Churchill Downs allows cigars, but they must be in their original packaging. Be sure to travel with cigars properly using a travel humidor. We highly recommend investing into the best travel humidor: Cigar Caddy travel cases.

Final Thoughts: A Bucket-List Experience

The Kentucky Derby is more than just a horse race—it’s a week of celebration, luxury, and timeless traditions. Whether you’re watching from the infield, a grandstand, or a VIP suite, expect fast horses, fine bourbon, and premium cigars to be part of the magic. If you plan ahead and budget wisely, you can tailor the experience to fit your style—whether you’re going all out or keeping it simple.

Whether you’re celebrating a big win or just soaking in the atmosphere, having the right cigar accessories is essential. Keep your cigars fresh with a travel humidor, ensure a perfect cut with a cigar cutter, and light up effortlessly with a premium cigar lighter. For those hosting Derby parties at home, a well-stocked cigar humidor ensures your collection is ready for race day. Pair your cigar with a fine bourbon, place your bets, and enjoy the ultimate Derby tradition!