The Kentucky Derby, only known as “Derby” in Kentucky, offers one hell of a time.

But you will enjoy it a lot more if you prepare for it in advance, gathering the things you need for the event before you travel.

I went to the historic Derby number 145 in May 2019 and want to relay what I learned about how to maximize this day in terms of value cost and the experience.

No reason to overpay!

Follow my lead, and I believe you’ll have a calm, stress-free, and cost effective day at Derby when you go. To help you master travel to the Derby, and many other destinations, check out our guide to the art of travel planning.

Table of Contents:

1. Buying the Clothes to Wear
2. Tickets
3. What I Did (In my Ticket Strategy)
4. Lunch
5. When It Rains, It Pours
6. What Else Not to Forget
7. Parking
8. What To Know Going into the Race(s)
9. Placing Your Bets
10. Events to Pair The Derby With
11. Where To Stay
12. Set A Budget

Buying Derby Wear

Do not wait to buy the clothes that make up your Derby outfit until days before you arrive in Kentucky.

The prices will be up-charged right around Derby week because of the supply and demand for them in local stores or online.

The solution: Buy them way in advance.

This is a tricky outfit comprising color combinations and accessories you most likely do not have in your closet.

It also saves you time so you can enjoy your Kentucky visit without the hassle of needing to include clothes shopping to cut into your trip.

Bring Your A-Game

You want to make sure you’re looking brilliant from head to toe!

I usually would not advocate caring about what other people think, but in this case, if you don’t want to feel out of place, there is no such thing as being overdressed for Derby.

Ditch Denim

Derby day is a day for spring dresses (both long and short), suits, leather shoes and heels.

If you insist on wearing pants, make sure it’s fancy and includes eye-catching accessories.

Jeans won’t cut it based on the outfits I saw.

Bold, Bright, Blossom

The brighter the better, as it is that type of fashion showcase.

Pastels, pinks, yellows, whites, baby blues are all nice choices.  Spring is your canvas.

Look to spring flowers and shades in your bold clothing patterns to stand out or fit right in, whichever you prefer.

**DON’T** Wear High Heels

Although my opinion goes against many others’, this is not the day to be uncomfortable walking around.

On Derby day, you will walk a ton, possibly in dirt and mud with the trend it has rained on Derby day, and you will stand most of the day.

Although I saw thousands of women and looking excellent in high heels, they did not look comfortable walking around and standing for eight hours.

For footwear, dress for comfort.

Yes, there is the argument you need to be elegant from head to toe in whichever style you enjoy. High heels, if a priority, is as crucial as the hat you choose, so go for it if you can handle discomfort.

If you choose heels, I read that getting a pair of Solemates High Heelers for your heels helps prevent you from sinking in grass, dirt, or getting your high heels caught on cobblestone or pavement cracks.

Men Shouldn’t Be Afraid to Wear Unique Color and Suit Patterns

Men will want to choose bow ties over standard neckties. Loud, fun socks and well suited hats along with excellent-looking cufflinks –> perfect!

Take spring fashion to the next level, push the envelope and avoid playing it safe!

Get just as dressed up and decked out as the ladies!

Sun-drenched, tropical colors in bold stripes or busy plaid and bright pastels steal the limelight.

Although, if you want a more polished look, a classic navy or seersucker blazer is always in style.

Men could turn to sun-drenched pants in vibrant colors like Key Lime, Ocean, Bermuda Pink, and Citron.

Any of these colors paired with the right shirt and blazer will make you stand out.

A great dress shirt in a complimentary color will go a long way. Grab a fun gingham or striped shirt to turn it up. This is the one day of the year where “more is better.”

The jacket brings everything together and you can’t go wrong with the classic navy blazer. If you want to have a little fun on top though, a nice chalk stripe can make the ladies’ big hats turn.

The 3- button side vent is more polished than the 2-.

For shoes, there are many types of loafers out there. You should wear them without socks.

Top it all off with a fedora or bowler hat for the complete Derby look. Most men’s Derby hats are solid and inspired by the style from the Roaring Twenties (1920s).

Women (and Men), Show Off Your Elegant Jewelry

“You can show off elegant pearls and costume jewelry, or take your own accessories to the extreme with bows, broaches, scarves, hats, earrings, flowers and more…

…You’re all on the red carpet today, you will want to give them something to remember!”

Source: TheSolemates.com

Choose the Hat First, THEN Pick the Clothes to Match It

For Women:

• Hat can be both large and over-the-top,
• Or paired with the dress as an accessory,
• You can’t go wrong with the hat you choose, which is one of the best parts about this day!

For Men:

• Solid in color.

I thought Derby was Mostly about the Races, but I was Wrong

It’s the fashion!

Tickets

Book your Trip without Derby Tickets

In my case and most other cases, prices drop like a rock in the days leading up to the Saturday, especially if rain is in the forecast.

Even though I can’t predict the future, it has rained at half of the 145 Derby days.

The Tickets I Wanted

• 1st Floor Grandstand- MY  RECOMMENDATION : These are bleacher-style seats, no backs and typically the best value seat option. The further away from the finish line the less it will cost.
• It is a reserved seat and trackside.
• You won’t get full-track views but it really doesn’t matter. The crowd there is terrific.
• Take note, make sure you look at the section numbers.
  • Seats in 128, 127, etc. are way on the end of the grandstand.
  • Although the Derby will take off right in front of you, your views of the rest of the track are fairly limited.
• The best reason to get a reserved seat is you do not have to arrive early.
  • It is a long day, with the big race starting at around 6:30 PM.
  • No need to arrive before noon even though gates open at 8 AM.
  • Besides a couple of races you are not missing much at this point in the day.

In my case, I compared what the resale ticket market looked like (for a grandstand ticket) a month before, a week before, a day before, and the morning of.

A Month Before

Average of $485 per ticket.

A Week Before

Average of $400 per ticket.

A Day Before (with rain expected in the forecast)

Average of $200 per ticket.

Same Day

Better seats, closer to the finish line than I expected, for $140!

What You May Not Want To Do Your Only Time Going

The Infield. Yes, the Infield is lots of fun, it’s fratty and young, BUT, on a rainy day, it is super muddy out there. It’s a lot like Mardi Gras. Most importantly-you do not get a seat.

The fashion and comfort gets negated by the dirtiness.

It’s less expensive (under $100), but way more crowded, the view is limited, and in my first and probably only time there, I wanted to get reserved seats and be part of the more “refined” crowd.

What I Did

I grabbed a $140 reserved seat ticket.

By waiting til’ the day of, I saved over $345 to be in the heart of the action. I knew I was going anyway, so I used the rain in the forecast to leverage the battle to get affordable tickets.

Lunch

I would suggest you plan on placing an order at any of the restaurants in town selling box lunches for the track. You may also pack your own in clear bags.

Saves money, time in food lines and gives you a better quality meal than you would find inside the facility. The food did not look that great and was expensive.

If you want to try a Mint Julep, skip the $15 one at the track and order a much better one for less at a fine bar in town.

When It Rains, It Pours

Knowing this, you’d think you should bring an umbrella with you to Derby, right?

They do not allow umbrellas at Churchill Downs.

Bring a clear poncho to cover(and still show off) your fancy outfit and hat should it rain. Do not forget this.

What Else Not to Forget

• Cash for food, drinks and wagering.
• Sunscreen if it’s sunny, a sweater if it’s chilly (and a poncho if it looks like rain).
• 

  With rain in the forecast you can’t let those fancy shoes get ruined!

• Snacks or a boxed lunch. If you keep it in a bag or a container, make sure it’s clear and smaller than 18 inches by-18 inches.
• Your own bottled water or soft drinks in a sealed, clear, unopened bottle.
• A small towel. On the bleacher-style seating, sitting on the towel will keep your pants/dress clean.

Parking

If you are driving, you have two options:

1. Park at Cardinal Stadium, then make the short walk to Churchill Downs.
2. Park in the residential neighborhood surrounding Churchill Downs, then walk to the track.
   • Don’t get sucked in to expensive parking lots of $25 and up.
   • People will offer their driveways for $10 in most cases.

What You Should Know Going Into the Race

20 Three–year-old thoroughbreds gallop around the track for 1.25 miles at 35 MPH carrying 112 lb Jockeys.

The Jockey receives 10 percent of the horse owner’s winnings.

Derby is widely known as “The Greatest Two Minutes In Sports.”

Justify and American Pharoah won the Triple Crown in 2018 and 2015, respectively.

1904 – The red rose became the official flower of the Kentucky Derby.

1925 – New York sports columnist Bill Corum famously nicknamed the Kentucky Derby the “Run for the Roses®.

Each year, The Kroger Company sews a garland of over 400 red roses into a green satin backing with the seal of the Commonwealth on one end and the Twin Spires on the other.

In the world of sports, there is not a more moving moment than when the horses step onto the track for Derby post parade.

• The band strikes up “My Old Kentucky Home.”
• 160,000+ people sing along.

“My Old Kentucky Home,” by Stephen Foster — Lyrics

The sun shines bright in the old Kentucky home,

Tis summer, the people are gay;

The corn-top’s ripe and the meadow’s in the bloom

While the birds make music all the day.

The young folks roll on the little cabin floor

All merry, all happy and bright;

By’n by hard times comes a knocking at the door

Then my old Kentucky home, Good-night!

Weep no more my lady.

Oh! Weep no more today!

We will sing one song for the old Kentucky home

For the old Kentucky home, far away.

The Mint Julep

The Mint Julep has been the traditional beverage of Churchill Downs and  Derby for nearly a century.

That’s a feat that requires over 10,000 bottles of Old Forester Mint Julep Ready-to-Serve Cocktail, 1,000 pounds of freshly harvested mint and 60,000 pounds of ice.

The Old Forester Mint Julep Recipe

• 2 cups sugar
• 2 cups water
• Sprigs of fresh mint
• Crushed ice
• Old Forester Straight Bourbon Whisky
• Silver Julep Cups

Placing Your Bets

Use The Churchill Downs Betting App/Twinspires.com

If you are at the Derby and are planning to place some bets, the lines can get loooooong.

The solution: bet online from your seat to skip the lines!

The app sometimes gives you a free $10 to use to bet as a welcome bonus.

Straight Wagers

Remember, with a straight wager, you only bet on one horse.

My suggestion is to stick to win, place, or show.

Don’t make your bets too complicated or the race won’t be fun for you.

• Win–You’re betting that your horse will come in first place.
• Place–When you bet on your horse to “place,” you’re betting that he will come in first OR second. Payout for a place bet is less than a win wager, but you have the security of being able to cash in if your horse finishes in the top two spots.
• Show–You’re betting that your horse will come in first, second, OR third. Since you’re hedging your bets, you have a higher chance of winning, but the payout for a show bet is substantially less than a win or place wager.

Exotic Wagers – In My Opinion, Are Usually Sucker Bets

Exotic wagers allow you to bet on multiple horses in a single bet, allowing you to increase your profit potential.

They’re much harder to win than straight bets, can get expensive if you’re not careful, and require much more skill in handicapping horses.

Exacta–You’re betting on two horses to come in first and second in an exact order.

Trifecta–You bet that three horses will finish in first, second, and third in an exact order.

Superfecta–You bet that four horses will finish, first, second, third, and fourth in an exact order.

Factors to Consider When Picking Your Horse(s)

Jockey

• The experience of the Jockey is huge. Some fans and experts consider Derby to be a “Jockey’s Race” because of the need to navigate thru a crowd of 19 other horses.

Surface Type

• Horses perform differently on each type of surface. Some horses love dirt tracks, some like Turf (Grass). Some do well on Firm (dry) tracks and some do well in Sloppy conditions (wet) .The race day program tells you each horse’s past performance on the different surface types.

The Odds

If you’re looking for an easy way to handicap horses that gives you a good chance of a small return on your money, just bet the race favorite to show. It works 67% of the time.

If you bet the favorite to place, you’ll win 53% of the time.

If you bet the favorite to win, you’ll win 1 out of every 3 races on average (33%).

What to Say to the Teller at the Betting Window

1. Race number
2. Amount of your bet
3. Type of bet you’re placing
4. Horse’s assigned number

For example: “Race seven, $2 to win on number 4 or ‘on the 4’.”

Do Not Throw Away Your Betting Ticket Until the Race Results Become “Official”

Some who had wagered on Country House to win immediately tossed away their tickets at the close of the race, before Maximum Security’s disqualification, only to then scramble and frantically look around Churchill Downs for their betting slips (if it wasn’t ripped up already).

The Key Events to Pair Derby With

To make your Derby experience complete, go to the exceptional Champions’ Day and Derby Museum.

Champions’ Day

It’s Derby Week’s Newest Event.

Champions Day highlights the history and the sport of the Kentucky Derby!

• Meet legendary jockeys and trainers and gain industry expert insights into Derby Week betting.

Event Highlights Included from this past Derby…

Autograph Session with Bob Baffert, Mike Smith, Steve Cauthen and Jean Cruguet.

• Derby Week handicapping Seminar
• Triple Crown Vault Photo Opportunity by the Kentucky Derby Museum

Mike Smith – The Hall of Fame jockey won aboard Justify in 2018.

Bob Baffert – Trained 2015 winner American Pharoah and 2018 winner Justify.

• His horses have won five Kentucky Derbys, seven Preakness Stakes, three Belmont Stakes and three Kentucky Oaks.

–   Steve Cauthen–known as “The Kid”, he became the youngest jockey ever to win the Triple Crown aboard Affirmed in 1978.

–   Jean Cruguet–Rode Seattle Slew to Triple Crown victory in 1977.

–   Elliott Walden–President & CEO, WinStar Farm and owner of 2018 winner Justify.

The Triple Crown Vault Photo Opportunity gave fans a chance to see –and have their photo taken with – trophies and other memorabilia from Triple Crown Winners War Admiral, Citation and Sir Barton.

• War Admiral 1937–Jockey Charley Kurtsinger’s  Preakness Jockey Trophy.
• Citation 1948 –Kentucky Derby saddlecloth and trainer Jimmy Jones’ Triple Crown Trophy.
• Sir Barton 1919–The Belmont Stakes Presentation Cup awarded to the first Triple Crown

You Will Hang with the Knowledgeable Locals

Many locals go to Champions’ Day and enjoy Churchill Downs without the chaos of Derby Day.

Go to the Derby Museum at Churchill Downs

This museum has an incredible surround screen presentation you won’t want to miss, “The Greatest 2 Minutes in Sports.”

• Lots of displays and interactive exhibits.
• Some are permanent and others are special exhibits.
• Walk through a starting gate, call a race, ride a simulated race, learn how to bet, see fashions through the years.
• With two floors of interactive, family friendly exhibits, the Museum takes visitors through every stage of a Thoroughbred’s life, from birth to the First Saturday in May.

Learn about all the great history of the race dating back to the inaugural running in 1875 to our most recent Kentucky Derby champion and experience all the traditions that have transformed the race into what it is today.

Don’t Make the Luxurious Derby Experience Topsy-Turvy. 

Thoroughly soak in this one-in-a-lifetime event as a result of some smart planning and prep beforehand!

Where To Stay

When you visit the Kentucky Derby racetrack, you need to consider where to stay. While Louisville, Kentucky is home to some spectacular, unique, and vintage hotels, it is unlikely these are feasible during the derby. As the derby approaches, nightly rates at hotels skyrocket. At the same time, vacancy rates drop severely as more and more tourists come to town. To find reasonable lodging accommodations, it is best to get out of the city altogether. Consider surrounding towns like Lexington Kentucky. Roughly 70 miles away, the ride to Lexington crosses the famous Kentucky Bluegrass, making a spectacular ride. To maximize your lodging strategies in every destination, check out our recent hotel travel guide.

Set A Race Day Budget

Now, you are ready to set a budget to save money on the Kentucky Derby race track. Remember, you can have a great time on the track even while keeping a budget. Set a maximum amount to spend on betting, food, and drink. Say $50 to be conservative, or $100 if you want to spend a little bit more. Take out all the cash beforehand to avoid deviating from your budget. This way, you can avoid the constant $3 or $4 ATM fees. Certainly, setting a budget is key to have a good time without letting the Kentucky Derby race take control of your wallet. If you didn’t make it out last year, check out our post on the 2020 Kentucky Derby COVID-19 version.