How to attend the Kentucky Derby: Comfy shoes, hats, tickets and more insider tips
Upon conjuring the notion that I wanted to attend the Kentucky Derby in 2010, a Louisville-based friend offered me the sagest piece of advice that still rings true today: don’t complain. Your feet will hurt. It will be expensive. It might rain. Odds are you will lose more money than you will win.
But it is also unlike any other sporting event this country has to offer, a complete sensory overload of sound, noise and bourbon that will require you to put your head on a swivel to take it all in. The race itself takes two minutes; the moment will stay with you for a lifetime.
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Along with patience, it takes planning and organization to pull off a Kentucky Derby boondoggle. After nine trips over the last 13 years, I won’t say I’ve mastered it; but I do have some ideas.

Traveling to Louisville and hotels
Book early — like now. The Derby is always a hot ticket, and getting there is not cheap. If you’re aiming toward 2024, be especially mindful. Next year marks the 150th running, which means it will be bonkers.
Hotels
The earlier you can commit the better — for options and pricing. Downtown will be the most expensive, but Churchill Downs is a drive from anywhere. Absent a hotel shuttle, you can purchase parking through kentuckyderby.com, or frontside tickets (more on that below) include parking at the nearby Expo Center. But the point is, there’s no need to be downtown if you can find a cheaper hotel on the outskirts.
Airfare
Same rules apply. Book early.
Insider tip
Check out flights into and out Cincinnati, Lexington and Indianapolis, each no more than a two-hour drive to Louisville, and considerably cheaper than flying into Louisville.
If you can, stay an extra day. Prices plummet on Monday.
Give yourself time on Sunday. Derby day is a marathon not a sprint, and those early-morning flights are less expensive for a reason. No one wants to wake up that early on the day after Derby.
Regardless, give yourself extra “getting to the airport” time if you’re flying out of Louisville post-Derby. It’s a small airport trying to process a lot of people.
When to arrive in Louisville
So it used to be — not too long ago — that the Kentucky Oaks was for the locals, the calm before the sea of outsiders stormed in through the gates. Then folks got wise to the fun of Oaks Day, and the Friday crowds swarmed to near the numbers of Saturday. Which, of course, begat Thurby, the new locals day. Except now, some folks arrive Thursday as well. Consequently, live racing begins on Tuesday of Derby week, with 502’sDay, and stretches through Saturday.
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Ideally, arrive by Wednesday night or Thursday. Hit the track for Thurby to acclimate yourself. Get gussied up for Oaks on Friday and then arrive feeling like an old pro by the Derby on Saturday.
Insider tip
On race day, arrive early. Derby post time is not until after 6 p.m., but live racing begins at 10:30, and the gates open at 9. You might as well get your money’s worth and reduce the hassle of traffic.
Do not rush out after either the Oaks or the Derby. Everyone will flock to the betting windows and then out the gates … and directly into a snarl of traffic. The last race on Saturday is at 8:30 p.m. Wait it out. Not only will you avoid some of the chaos, but when everyone bolts for the doors, you can easily wind yourself down to the good seats. My first Derby we wound up right on the rail for the late races, practically an arm’s length away from the horses.
Kentucky Derby Tickets
It’s not complicated, really. The more you spend, the better your seat. Tickets are on sale at kentuckyderby.com, and your typical secondary markets. They are not cheap.
Repeat: they are not cheap.
Infield
Think all-day tailgate party. Pack a lawn chair or blanket and watch the races on a big screen. General admission tickets are the cheapest way to see the Derby and run $87 this year for both Oaks and Derby. But you’ll only catch a fraction of a glimmer of a live horse and instead watch the races on that big screen. There is no access to the frontside — not even the paddock area — and the crowd tends toward that tailgate vibe, mostly college-aged.

Frontside
Plan to spend no less than $700 per ticket, and that’s probably on the low side. Ticket prices vary depending on location, location, location — near the finish line cost more, for example. Frontside tickets also give you access to the paddock, a great spot to see the horses up close as they get saddled before each race. It’s also a fun spot to watch a race or two on the big screen or take in the splendor all around.
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The good news: tickets on the frontside are all-inclusive, meaning your ticket price also pays for your food and drink all day. Yet another reason to come early.
Insider tip
If you’re paying for a seat, make sure it’s undercover. The lovely seats in the bright sunshine are fantastic … except when it pours. Then you wind up huddled under whatever piece of roofing you can find, your hat ruined and your seersucker striping bleeding together. Undercover seats offer just as good a view, and you are still free to mill about to the sunshine — visit the paddock and so forth.

What to see around Churchill Downs
It’s a long day, and while mint juleps or Lilys (the vodka drink of the Oaks, also served on Derby day, for those who are bourbon averse) can sustain you for some time, it’s good to wander around.
If you are on the front side, there are vendors — for drinks, souvenirs, stuff everywhere — not to mention the shop and museum on site. The lines will be long and the prices high, so do with that what you want. Otherwise, a requisite shot with the twin spires behind you is practically mandatory. Other options: pose in front of the paddock statue of Aristides, honoring the first Derby winner, or stop by the statue of Barbaro, the 2006 Derby winner who battled injury and infection a year after his win, outside of the front entrance.
In the paddock, looking up to the porch seats and looking for celebrities is always fun. Tom Brady is a regular on Oaks Day.
What to wear and hats
Of course, hats, sundresses, suits, and bow ties, but wear comfortable shoes for the love of all that is holy. It’s a long day on your feet, with some tricky terrain. At the very least, pack an extra pair of flats or flip-flops.
This is not a women’s only event; men are encouraged to dress out, too. Seersucker and fedoras are popular — think pastels or navy.
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The only rule is there are no real rules. From classics to caricatures, you will see it all on the Churchill grounds.
Insider tip
Prior to the Kentucky Oaks, breast and ovarian cancer survivors participate in the Survivors Parade, so pink is always a smart attire choice for Friday.
The Louisville secondary market is loaded with gently worn hats. Check Facebook marketplace, online thrift stores, eBay and so forth.
You can also pre-order hats in Louisville, available for pickup upon arrival.
You can bring bags (under 12 inches) onto the grounds, so along with extra shoes, don’t forget sunscreen and rain ponchos, just in case.

How to bet on the Kentucky Derby
Making that first bet can be intimidating, so remember the order: dollar amount, bet, and horse number. $2 to win on the five, or $3 exacta box with the 3 and the 2.
All transactions are cash only. Lines at ATMs can be long. Bring your cash with you, and I hope you don’t have to replenish.

Fortunately, the tellers are patient, so don’t worry if you don’t know what you’re doing, but be prepared once you get to the window. No better way to tick off your fellow bettors than to peruse your program while leaning up at the window.
(Top photo: Brian Spurlock/Icon Sportswire, Ezra Shaw, Jamie Squires/Getty Images; Photo of fans on the infield: Michael Reaves/Getty Images; Bill Belichick by: Rob Carr/Getty Images; woman in hat: Brian Spurlock/Icon Sportswire via Getty Images)
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