Like any big, bucket-list event—the Masters, Mardi Gras, the Super Bowl—attending the Kentucky Derby takes more planning than just buying the ticket. The sea of hats, the clamor at the betting windows, the haze of the infield, the maze of traffic all make the most exciting two minutes in sports “less a sporting event and more like the biggest party you have ever been invited to,” says Edward Lee, the chef behind Louisville restaurants MilkWood and 610 Magnolia. “For one grand afternoon, gentility and debauchery go hand in hand.” Navigate that julep-fueled marriage of the high and the low with ease with these tips from Bluegrass State insiders.
Dress for Success
“You will likely have to park fairly far from the entry gate to the track. Ladies, do not wear your high heels to make the journey on foot from your car to your seat. Carry a tote bag with your fancy shoes and wear something comfortable into the track. Don’t bring an umbrella; it will be confiscated at the gate.”—Julian Van Winkle, president, Old Rip Van Winkle Distillery
“Travel with rain boots—you’ll be glad you have them! If it’s going to be sunny out, wear an actual hat (instead of a fascinator); the sun shade will be necessary.”—Conley Crimmins, senior integrated marketing manager, Garden & Gun
Nerissa Sparkman
“Dress sharp but comfortable. You never know what party you will get invited to or where you will end up. It may be a long time before you get to change out of that Derby outfit so make sure you are okay with staying in it all day and night.”
—Edward Lee, chef-owner, MilkWood and 610 Magnolia
“Once your hat is on, keep it on. Pin and style your hair underneath your hat so you can remove it at dinner and have a whole new look.”—Peggy Noe Stevens, entertaining expert, founder of the Bourbon Women Association, and the world’s first female master bourbon taster
“Bring a rain poncho—because it always seems to rain on Derby day—and in keeping with that, suede shoes may not be a good idea.”—Marc Salmon, resident historian, the Brown Hotel
Pack the Essentials
“Make sure to check the Churchill Downs website for bag size restrictions. And remember to pack cash for betting, sunscreen, a poncho, and a pair of flip flops or flats. Derby is a long, fun day out in the elements with lots of walking.”
—Annie Pettry, chef-owner, Decca
“Pack an empty canvas bottle carrier to stack your glass keepsake julep cups from the track and transport them home safely. Bring back-up pens to write on the programs because inevitably everyone loses theirs. Instead of packing a lunch, graze like the horses—think picnic food like pimento cheese and Benedictine spread.”—Peggy Noe Stevens
“Paper money is the name of the game at C-downs. Don’t bother with a card. The ATM lines are absurd. Bring around $200 in cash (and then whatever you’d like to bet).”—Conley Crimmins
“If you don’t want to lug home your souvenir glasses after the race, stop by Kroger and pick up a fresh set for a few dollars.”—Colleen Glenn, associate publisher, marketing, Garden & Gun
Place Your Bets
“A fun way for a big group to enjoy the day and not bet a whole lot is to have everyone throw in a few bucks and start a rolling show pool. What is that you ask? Each race, people take turns picking one horse in the race to show, meaning the horse has to finish in the Top 3. If the horse does, you win. And each race you continue rolling your entire pool of winnings onto another horse to show. If you lose, you simply start over. And if you don’t lose, well, it can be a pretty good return on investment and keep you interested throughout the great day of racing.”—Chris Fallica, senior researcher, ESPN
“If this is your first horse race, brush up on your betting knowledge and lingo—read ‘What to Say to the Mutuel Teller’ so you’ll bet like a pro on Derby day.”—Annie Pettry
“Lines for bathrooms and betting windows are longest immediately after a race, so plan accordingly.”—Peggy Noe Stevens
Do a Practice Run
“For a slightly more casual vibe and smaller crowds, head to the track on Thursday, aka Thurby, and hang with the locals. Or check out Kentucky Oaks on Friday when the fillies run, and join the sea of pink-clad racegoers. Churchill Downs holds a ‘pink out’ on this day to bring awareness to the fight against breast and ovarian cancer.”—Annie Pettry
“In some ways, the best day you’ll have is Thurby—Thursday at Churchill Downs—or Oaks day. It used to be that the Oaks on Friday was the greatest day, because it was a relaxed townie day at the Derby. On Derby day, get there early. Watch every race.”—Wright Thompson, senior writer, ESPN; Garden & Gun contributor; author, The Cost of These Dreams
Photo: Greg Keysar
Kentucky Oaks.
Pick Your Pace
“We always tell the first-timers the same thing—it’s really a marathon. There are parties morning, noon. and night (and afterparties) for three straight days. If you want to last the entire weekend, you have to pace yourself. Eating and drinking like this is not for the faint of heart, and the locals know that moderation is the key to survival.”—Edward Lee
“Stay hydrated, and two mint juleps is one too many!”
—Brooks Reitz, former Louisville resident and Charleston, South Carolina, restaurateur (Leon’s Oyster Shop, Little Jack’s Tavern, Melfi’s) and founder (Jack Rudy Cocktail Co.)
“Arriving after 2 p.m. is a perfect time, as there is plenty of time to take in the fantastic racing and build-up to the big race. While at Churchill enjoy the buzz of the crowd, the people watching, and the spectacular equine athletes. As the Derby horses are in the paddock, be sure to find a good place where you can see the big screen and follow along with the singing of ‘My Ol’ Kentucky Home’—the goosebumps are only overcome when they spring from the gates and we watch the most exciting two minutes in sports.”—Price Bell Jr., Mill Ridge Farm
“The actual race starts so quickly and is over in a flash. Be in your seat at least thirty minutes before race time. Otherwise you’ll miss a lot of the pageantry of the race.”—Conley Crimmins
Andrew Hyslop
Don’t Forget to Soak Up Louisville
“The best tip of the day is to not rush—to enjoy springtime in Kentucky—because it is this setting that makes the Kentucky Derby so special. There is a lot of racing on the day, and oftentimes first-timers will feel an urgency to get to the track as early as possible, and by the time the big race happens, they are tired and not able to enjoy it. Louisville is a beautiful city and its parks are fabulous, especially in early spring. I believe a walk through Cherokee Park, followed by coffee and breakfast at Quills coffeehouse, is the best way to start Derby day. Around Quills is great shopping and dining as well; wrap that up by 12:30 or 1, and then go change into your hat and head to the track.”—Price Bell Jr.
“There is something magical about the Kentucky Derby, and the best way to understand it is to be in Louisville during the weeks leading up to Derby week. Flowers are in bloom, the sun kisses everything in a verdant green. Everyone is a little prouder, a little more festive, and excited for what is the best weekend of the year for Louisvillians. We are proud of our city, and for one weekend out of every year, we are the envy of the entire world, and that is something that is never lost on us.”—Edward Lee
