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Derby Daze: Navigating the race at Churchill Downs

Long before the first Super Bowl, there was the Kentucky Derby. It’s the country’s oldest continuous major sporting event in the United States. 

From the hats worn on Millionaire’s Row to the party with thousands of people in the infield, the festivities and excitement of the Derby extend exponentially beyond what is known as the “most exciting two minutes in sports.”

Doug Dearen, a Louisville native and the owner of Derbybox.com - a travel company focusing exclusively on packages for the Derby, will be attending the events next Saturday, May 5th as his 33rd consecutive Derby. He says if you haven’t been before, there’s still time to plan your visit to Churchill Downs.

“It’s more than that (the Super Bowl) because there’s so much history and tradition involving the Derby,” Dearen said. “This is the 138th year.. Now, more than ever, it involves almost two weeks of activities and festivities and parties," said Dearen. "People go to the races on Thursday, Friday, and Saturday. 150,000 people attend every year. It’s sport and it’s fashion and it’s excitement and it's a party. All those many things wrapped into one.”

Tickets for this year’s Derby are still available. Dearen says get your seats soon as many if not most sell out at least three or four days before the race.

“If you want to have a good seat, you need to be in a box seat or in the stands,” Dearen said.

For those who want one of the best seats, Millionaire’s Row is the place to be. Dearen says those tickets can cost around $4000-$5000 each.

“Millionaire’s Row is obviously indoors,” Dearen said. “It’s a dining area where there are round tables and a gourmet buffet. You go out on a private-type balcony to watch the races - designated just for those ticket holders. That’s where a lot of the movie stars are. People like Ashton Kutcher, Tom Brady and Michael Jordan.”

For those more concerned about having a good time instead of seeing the race - Dearen says there’s even a place for you.

“You can pay $45 at the door and get into the infield, which is a giant party,” Dearen said. “The infield is like anything and everything you can imagine. Streakers, mudslides - it’s kind of like mardi gras in the infield. Those people hardly ever will see a horse because there’s no real viewing but they’re there to soak up the party and the atmosphere and everything else.”

Getting to Louisville

Probably more difficult than even getting a ticket into Churchill Downs at this point is getting a flight into Louisville. Even booked well in advance, flights into the home of the Derby are difficult and often expensive for the weekend.

“It seems like if you fly on the Friday, you have a better chance than the Thursday,” said Lauren Sullivan, the content and social media editor for Cheapflights.com. 

While most travelers fly into Louisville on Thursday and out on Sunday, Sullivan recommends extending the trip by a day or two to avoid the peak travel days and possibly get a better deal.

If you haven’t already booked flights for this year’s Derby, flying into Louisville directly may be out of the question. The Cheapflights.com travel expert also suggests flying into a nearby city.

“If you’re going with a group, consider one of the alternative cities because you could rent a car, split the cost of the rental car and drive the remaining few hours,” Sullivan said.

She suggests flying into Lexington, Kentucky (about 1.5 hours away by car); Cincinnati, Ohio (about 2 hours away by car); Indianapolis, Illinois (about 2 hours away by car) or Nashville, Tennessee (about 3 hours away by car).

“Instead of making a whole trip in Louisville, go to Nashville,” Sullivan said. “The best prices we have currently are into Nashville. Then, if you are in Nashville, you’re getting a whole vacation out of it instead of flying in for just one event.”

Staying near the Derby

Most hotels in Louisville require a three-night stay over the Derby weekend. The rooms are often booked out weeks, if not months in advance.

While almost all hotels in Louisville are already sold out for next weekend’s event, Hotels.com vice president and general manager for North America, Victor Owens, says there are still some options nearby.

“For those who decide to attend last minute, customers can still find good deals on hotels.com and through our mobile booking app,” Owens said. “We recommend looking at nearby cities including Lexington, Frankfort, Fort Knox, and Elizabethtown and even across the river in Indiana.  Customers can search hotels by proximity to the Churchill Downs Racetrack so you can ensure you are close to the action. And, don’t forget to call ahead for lunch and dinner reservations for great locales like Proof on Main or Lynn’s Paradise Café to make the most of your Derby experience.”

Fitting in from Head to Toe

The Derby, which is the first leg of the triple crown, is also a time to crown your head with your best brim.

“Most people do dress up,” Dearen said. “The ladies wear nice dresses, big fancy hats. Men wear sport coats and ties. You don’t have to. It’s not required, but to get into the spirit of it - most people do.”

For those purchasing a hat for the first time to wear to the Derby, national etiquette expert and the owner of The Protocol School of Texas, Diane Gottsman, says the headwear should be functional, as well as a statement.  This goes for women and men.

“You want to take into consideration your own face and body style,” Gottsman said. “You don’t want it to overpower you.”

And don’t forget to pick out your outfit for the weekend at the track by starting with your hat. Then, compliment it with a matching sundress and light jewelry.

“It’s all about feeling comfortable in what you’re wearing,” Gottsman said. “You have to own it, feel comfortable and self-confident because confidence shows.”

Make sure if you are flying to the Derby that the hat doesn’t get smashed along the way.

“Get one of those fancy hat carriers as your one personal item,” Sullivan said. “I don’t recommended checking baggage for a weekend, especially if you have a fabulous hat. Invest in a great piece of carry-on luggage that is hard and can’t be crushed or a fancy hat carrier and substitute that instead of a laptop.”

Even if you won’t be traveling to the Derby this May, Gottsman encourages women across the country take part in the fashionable Saturday event.

“The bottom line is you don’t have to be at the Derby to enjoy the festivities,” Gottsman said. “You don’t have to miss out on the fun of wearing and creating your own hat. You can have a girls’ party or couples’ party. You can make your own social event.”

Local Tips

If you’ll be in Louisville, locals says you don’t want to miss the events and parties leading up before the race.

“There’s a big party on Friday. It’s called the Barnstable Brown Gala,” Dearen said. “That’s where all of the celebrities go... It’s Louisville’s night at the Oscars kind of thing.”

But don’t expect to just show up and walk in. You must purchase tickets in advance, such as from Dearen’s Derbybox.com.

If you like bourbon, Dearen says visitors are in for a real treat. He says everyone must try the race’s signature drink, a mint julep.

“It’s part of the tradition,” Dearen said. “I don’t think I could not have one on Derby day. It’s something you just have to do.”

Betting is another must for those going to the Derby. Dearen says his best advice is to place your money on your first inclination.

“And also bet on things like colors you like or names your like or numbers you like because when those things win and you haven’t bet on them - you feel horrible,” Dearen said.

Finally, Dearen says get ready to be wowed even after the race is over.

“After the Derby itself, the most significant moment is when the horses walk onto the track for the post parade,” Dearen said. “That’s where everybody stands with a mint julep in hand and they play ‘My Old Kentucky Home.’ It’s a ballad and people stand, sing and get emotional. You have to have your betting done. Your food done. You want to be ready.”

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