Attending the Kentucky Derby for the first time? The iconic race is a must-see on May 2, 2026. Locals know all about Derby traditions—like making mint juleps, picking the best seats at Churchill Downs Racetrack, and celebrating with the right dinner reservation. To help you enjoy the event like a pro, here are seven key tips for this year's Kentucky Derby.

1.  Prepare for both sunshine and rain at the Kentucky Derby

Experienced Kentucky Derby attendees monitor the weather forecast closely and prepare for rain or cold temperatures accordingly. Although pleasant conditions in the low 80s are ideal, weather in Kentucky remains unpredictable. It is advisable to pack a poncho if rain is expected and to have arrangements for colder weather, as snow has occasionally fallen on Derby Day. Also, remember that umbrellas are not allowed inside the gates. Coordinating an appropriate coat with your Derby hat is recommended should cooler conditions arise.

Additionally, wearing a fascinator or hat is customary at the 2026 Kentucky Derby, and this tradition extends to men as well.

2.  Avoid wasted time, extra costs, and stress by understanding what items are allowed and prohibited before you enter

Experienced Derby attendees are aware that the track event encompasses 14 races throughout the day, typically commencing at approximately 10:30 a.m. Given the extended duration and the likelihood of spending considerable time standing, it is advisable to prepare by bringing Band-Aids for potential blisters, sunglasses, travel-sized sunscreen, aspirin, an external phone charger, a foldable poncho (weather permitting), and a lightweight wrap or jacket for the evening.

It is important for newcomers to note that cash is required for placing bets in person. Although ATMs are available throughout Churchill Downs, it is recommended to arrive with sufficient funds and adequate space in a purse or pockets to securely store any winnings.

Prohibited items include umbrellas, backpacks, canopies and tents, coolers, illegal substances, and seat cushions exceeding 15 inches by 15 inches with metal arms or backs, zippers, pockets, or flaps, among other restricted articles.

3.  Acquire a Kentucky Derby glass to enhance your collection or for potential resale.

Don't be surprised if you spot race fans leaving the track with stacks of empty glasses. In Kentucky, it's common for Derby-goers to collect the special glasses their mint juleps and Oaks Lily drinks are served in at Churchill Downs, taking them home in neat piles. This has been a tradition ever since the mint julep became part of the Kentucky Derby; many people use these glasses for drinks at home throughout the year, while others store them carefully, as some older and rarer Derby glasses can fetch hundreds of dollars.

If you'd rather not carry your glasses home in your luggage, you can purchase Kentucky Derby glasses any time from the Kentucky Derby Museum.

4.  Beware the power of the Mint Julep!

The classic mint julep is potent! The iconic Kentucky Derby cocktail is mostly bourbon, with little else to dilute its strength. When made with 80-proof whiskey, it comes in at about 28% ABV (56 proof). So, please drink responsibly.

5.  Sort out your Kentucky Derby bets before you get in line

Make sure you look up how to bet on the races before you head to Churchill Downs during Kentucky Derby Week. Trust us, it's not as straightforward as it seems. If you're a beginning bettor, and are there in person, you probably want to avoid the self-service betting machines and mobile applications, instead opting for a mutuel window with an in-person teller.

Have your money in hand as you approach the teller, then state the race you're betting on, the amount you're betting, and the type of bet you are placing. Then, state the horse's (or horses') program numbers. It should sound something like this, "Churchill Downs, Race 11, $2 to win number 4."

Once you hand the teller your money, be sure to take the ticket and keep it in a safe place. If your bet wins, you'll need the ticket to collect your winnings.

You also can wager through the racetrack's online wagering platform, twinspires.com. You're required to create a username and password, but signing up is free and doesn't take much time. You can transfer money from your bank account into your TwinSpires account and then place your bets. A TwinSpires app is also available on smartphones.

With sports betting now legal in Kentucky, there are several sportsbook apps and sites that will take bets on the Kentucky Derby.

6.  Plan how you are going to get there well in advance

To make sure the day goes smoothly, it’s important to plan ahead and avoid common transportation pitfalls—think twice before assuming you can park at the track or relying solely on ride-share apps, and be sure to check your parking location and the latest drop-off points. Consider using a private shuttle service that has multiple pickup and drop-off times so you can arrive and leave when you want. Some local transportation companies will also offer group shuttle services that require a wristband purchase and a pickup-dropoff location outside of Churchill Downs. By organizing your travel details now, you’ll be able to focus on enjoying the experience and not scrambling at the last minute.

7.  Plan your Churchill Downs exit before the Derby

In 2024, approximately 156,000 attendees visited Louisville for the Kentucky Derby, temporarily making Churchill Downs the third-largest city in Kentucky. Due to the significant influx of visitors, transportation within the city, particularly between downtown and Churchill Downs, can be challenging.

Road congestion and modified public transit—primarily consisting of shuttle buses—necessitate preparation for walking at various points throughout the day. While the distance from the racetrack to downtown hotels is generally too great to walk, guests should expect to travel on foot between their seats and parking locations, shuttle bus stops, or designated ride-share areas.

To minimize post-event traffic delays, it may be beneficial to remain at the venue until after the last race, when crowds and road congestion typically subside. It is important to note that additional races follow the conclusion of the Kentucky Derby.

Conclusion

Attending the Kentucky Derby is a thrilling experience that requires thoughtful planning to ensure a memorable and stress-free day. By preparing your travel arrangements, understanding your wagering options, and anticipating the challenges posed by large crowds, you’ll be well-equipped to enjoy all the excitement that Churchill Downs has to offer. With these tips in mind, you can focus on soaking in the unique atmosphere, watching the races, and creating lasting memories at one of America’s most iconic sporting events.

Note: This blog is for informational purposes only and does not represent any endorsement by Pegasus.

Pegasus Global provides shuttle service and private transportation to all things Kentucky Derby 2026....

Looking to go on a bourbon adventure? Contact Pegasus today!

Pegasus is an Official Partner

Only Pegasus offers an unmatched blend of luxury and elegance in chauffeured & chartered services, personalized tours, and exclusive Kentucky Bourbon Trail's™ distillery experiences, all backed by 5-star reviews. We excel in providing top-tier transportation for distinguished events like Bourbon and Beyond, Kentucky Bourbon Festival, and Louder Than Life, ensuring a memorable journey every time.