Everything you need to know about the race ahead of its milestone anniversary
Next month brings the 150th running of the Kentucky Derby, the fastest, most exciting two minutes in sports. Since 1875, when a thoroughbred named Aristides wowed a crowd of 10,000 at the track that would become Churchill Downs, all eyes have been on Louisville the first Saturday in May. Of course, seeing the winner of the first jewel in the Triple Crown is just part of the Derby experience. Here’s a guide to everything you need to know about the race—and how to attend it in style.
Starting Lineup
Each year, 20 3-year-old thoroughbreds earn the chance to run in the Kentucky Derby—and securing a spot isn’t easy. To qualify, they have to compete in a series of designated races in the U.S, Europe, U.A.E., or Japan that’s fittingly called the Road to the Kentucky Derby. The top five finishers in each of these races are awarded points, and the 20 horses with the most points earn a spot at the starting gate come the first Saturday in May. While it’s too soon to say who’ll be running, insiders know to look at trainers. Keep an eye on horses trained by Derby regulars such as Todd Pletcher, Steve Asmussen, Brad H. Cox, and Kenny McPeek.
Horse Tales
Every horse who runs in the Derby has a story. Here are three winners with particularly notable tales to tell.
Whirlaway
The winner of the 1941 Derby, Whirlaway was a small chestnut colt with an unusually long tail that streamed behind him like the tail of a kite. He was a crowd favorite, thrilling spectators with his last-to-first bursts, but getting him into the gate was an adventure. He had a tendency to drift across the track when he ran, so his trainer devised a one-eye blinker with a tiny hole in it to limit his field of vision. The invention worked: Whirlaway won the Derby by eight lengths. His time of 2:01:40 would stand for 21 years, until Decidedly beat it in 1962.
Secretariat
Widely considered the greatest race-horse ever, this handsome chestnut set the Derby record in 1973, finishing in 1:59:40. He also set the records for the fastest Preakness and Belmont Stakes on his way to winning the Triple Crown. His outgoing personality attracted admirers, and he was smart enough to know what was going on, posing for cameras whenever he saw them. As for his name? It was proposed by the long-time secretary to his owners, because her previous job was with the secretariat at the League of Nations; most people called him Big Red.
Barbaro
This champion horse won the 2006 Derby in a runaway—nearly seven lengths ahead of second-place Bluegrass Cat—but it’s what happened next that captured the hearts of millions. At the Preakness, he shattered his right hind leg—a life-threatening injury for a thoroughbred. The media followed his eight-month struggle for survival, through various surgeries and complications, until it became clear his pain could not be managed, and his owners decided to end his life. A memorial was erected at Churchill Downs, featuring a life-size bronze statue of the horse in mid-stride, jockey on his back.
Top it Off
At the Derby, a hat is a must. Initially, they were worn both out of necessity—that Louisville sun is no joke—and for style, and the tradition remained. “If you’re not wearing one, you stand out,” says Jenny Pfanenstiel, the owner of Formé Millinery and The Hat Shoppe in Louisville and a five-time featured milliner of the Derby. “Your hat is the focal point of your complete look.”
In Pfanenstiel’s 16 years of handcrafting playful toppers—including for Michelle Obama, Oprah, and Madonna—she has seen trends come and go. “When I started making hats for the Derby, the big brim was certainly the hat everyone wore,” she says. “Fascinators became the rage after Kate Middleton got married.”
At Churchill Downs, though, “anything goes,” says Pfanenstiel, who also offers hat-making workshops. “You will see everything from elegant and simple fascinators to larger-than-life brimmed hats to plastic horses sitting atop their heads. I always look forward to seeing what people come up with.”
Drink Up
The mint julep became the official drink of the Kentucky Derby in 1939, but its roots stretch back much further. “In the 1800s, it was considered a morning drink,” says Elizabeth McCall, Woodford Reserve’s master distiller. “People working on horse farms or in the horseracing industry during this time period would wake up with aches and pains. You didn’t have aspirin, so you’d make a mint julep: bourbon to soothe your aches and pains, sugar to cut the alcohol, and mint to freshen the breath.” Many at the Derby still consider it a morning drink; after all, the bar opens at 8 a.m. (Fun fact: It’s Kentucky law that Louisville bars don’t have to close from Derby Eve to Derby Day.)
This year marks Woodford Reserve’s 25th year of being the official bourbon of the Kentucky Derby, and the brand is also a presenting sponsor. “Bourbon and horses are so deeply intertwined in Kentucky,” McCall says. “The Woodford Reserve Distillery is nestled among rolling horse pastures where these magnificent athletes are bred and trained. The same nutrient-rich water that gives great flavor and makes great bourbon is what helps horses grow to be strong athletes.” To celebrate the 150th running, the brand has created two special bottlings: the annual Derby bottle, featuring Kentucky native Wylie Caudill’s painting Adorned in Roses, and a super-luxe Baccarat edition, limited to 150 bottles. One person sure to score a bottle of the latter? The owner of the winning horse.
Sweet Finish
Derby-Pie®, a sugary, chocolate-and-walnut confection, is the ultimate Kentucky treat. Don’t try to order it at most restaurants, though; instead, ask for chocolate nut pie, Kentucky pie, Pegasus pie, or May Day pie. Why? Because the dessert’s creators, the Kern family, patented the name in 1969. They diligently protect their property, filing countless lawsuits against restaurants, cookbook authors, and websites. Fear not, however: You can order the pies online.
The Seating Chart
More than 256,000 people are expected at this year’s Oaks Day and Derby races. Here’s where they’ll be watching.
Clubhouse Boxes
A notch up from the Grandstand, these seats are six or eight to a box. (The prime area is on the third floor, overlooking the finish line.) The Clubhouse also offers better restaurants and bars and, crucially, more bathrooms.
The Grandstand
For views and an actual seat at a price that won’t break the bank, head to the Grandstand, which offers bleachers on the first and second levels, or boxes—with cover from the rain—on the third level.
The Turf Club
If you’re looking to spot celebs (last year’s attendees included Patrick Mahomes and Chris Pine), buy a ticket to this members-only lounge and dining room with views of the finish line.
The Mansion
Food from James Beard Award winners, Chanel makeup artists providing touch-ups, betting advisors, Paddock tours… this is true Derby luxury.
The Infield
These are the cheap seats ($85), though there aren’t actually any seats, and you can’t really see the races, except on the Jumbotrons. It is, however, the most fun place to be—a daylong party at which 80,000 of your closest friends start knocking back mint juleps at 8 a.m.
Girl Power
The Friday before Derby Saturday is known as Oaks Day, and the big event is the Longines Kentucky Oaks, the country’s most important race for 3-year-old fillies, which debuted on May 19, 1875. Rather than roses, the winning horse is given a blanket of lilies—fittingly called Lilies for the Fillies. The race has long been overshadowed by the Derby, but locals think of it as the classier of the two race days, and many attendees wear pink in honor of survivors of breast and ovarian cancer. (An annual Survivor’s Parade is one of the highlights of the day.) The Oaks even has its own drink: Instead of mint juleps, attendees toast with the pink Oaks Lily cocktail, a blend of vodka, cranberry, lime, and triple sec.
If You Go
Stay
Louisville’s best hotels are downtown, about a 15-minute drive from Churchill Downs. For quiet luxury, book a room at The Grady, which opened in 2021 in a medicinal bourbon apothecary from 1883. If you’re looking to keep the party going after the races, opt for Hotel Genevieve, which opened last spring in NuLu and boasts the city’s best rooftop bar. For a dose of Georgian-Revival glamour, you can’t beat The Brown Hotel (pictured above), which celebrated its 100th birthday last year and is also the birthplace of the city’s most famous dish: the gut-busting Hot Brown, an open-faced turkey sandwich smothered in Mornay sauce and topped with bacon.
Eat
Start your day off sweet with a glazed honey bun from Nord’s Bakery or tres leches pancakes at Con Huevos. Explore the city’s mainstays for lunch: The Irish Rover for fish and chips or Vietnam Kitchen for pho. At dinnertime, score a grill table to cook Korean barbecue at star chef Edward Lee’s latest spot, Nami (pictured inset); tuck into tacos at Guacamole Modern Mexican; or feast on bison empanadas at Louisville rapper Jack Harlow’s fave spot, Seviche.
Drink
A distillery tour is a must when you visit Louisville. At Michter’s Fort Nelson Distillery (pictured below), there are three tour options, plus you can fill your own bottle of Barrel Strength Bourbon straight from the barrel. If you really want to know how the good stuff gets made, book the Private Select Tour at Angel’s Envy—the largest distillery on downtown’s Whiskey Row—which includes a tasting of three expressions.
