By Russell Worth Parker, Editor at Large
Before the 2022 Breeder’s Cup, I had never been to a horse race. The closest I’d ever been was my grandmother’s annual insistence on picking a horse for each of her children and grandchildren then letting us know who won. It was a fun tradition for a far-flung family but now she’s passed, I don’t really gamble and, truthfully, I’ve never been much for organized events of any stripe, an irony for a retired military officer. Then Tom Beckbe invited me to Keeneland. I trusted previous Beckbe trips, with their history of fine company, fine food, and some of the finest duck hunting to which I’ve ever been exposed, to serve as a model. I was not disappointed.
But even more than my ever-expanding appreciation for the finer things, at Keeneland I discovered the magic of horseracing lies in the characters around the track, the history of the horses, and a culture born of the union of the two. Without a guide, a destination as rich in color and texture as the Kentucky Derby can be a blindfolded walk through a forest. With a guide it can be a transformative experience. My friend Andy Hyslop, a Louisville local who grew up in horse racing, is generous in all regards, but is particularly giving of his passions when sharing the people, places, and things he loves with a novitiate. If the Derby is the “Most Exciting Two Minutes in Sports,” I had 2,878 other minutes to fill in a weekend. Accordingly, I reached out to Andy for guidance on making the most of the Kentucky Derby.
Andy knows of my appreciation for good food, as does my tailor, who appreciates my appreciation. It was natural that I ask him to identify the quintessential dining experience for gastrophiles drawn to Louisville and the Derby. He did not disappoint.
Jack Fry’s, consistently found on “Best Of” lists, offers a nod to the importance of history in an event as venerable as the Derby. Jack Fry was a lovable rogue who welcomed all friends and gave food to the needy from his restaurant in Highlands. What’s a little backroom gambling and liquor between friends anyway? Jack and his wife Flossie founded the place in 1933 and ran it for almost forty years. Current owner Stephanie Meeks started there in 1996 and bought the works in 2008. The menu is lovely, but the enthusiastic local recommendation is the Shrimp & Grits.
Located in Harrods Creek, The Pine Room is a resurrected local favorite, perfect for folks looking to take a drive east along the Ohio River to escape the Derby fray. The original Pine Room caught fire in the late 1970’s, was renovated, and then burned completely to the ground. Four years ago, the Pine Room arose from the ashes like a phoenix thanks to visionary owner Augusta Holland. Located in shouting distance from the original, the reinvented Pine Room offers vegetarian, gluten free, and health-conscious options, but knowing my predilections, Andy offered, “The Buttermilk Fried Chicken - definitely the fried chicken.” You don’t have to tell me twice, but Andy did, so I know what I’m doing.
Proof On Main is found downtown in the hotel 21C. With the art, the food, the spirits, and the scene that develops around them all, you will find something here to surprise you, pleasantly. With apologies for the play on words, if you need proof, look to Chef de Cuisine Josh Bradley’s constantly changing, locally sourced menus.
If you somehow got to Louisville without an understanding of the cultural, economic, and experiential importance of bourbon, you will leave with one. Kentucky’s six major distilleries produce most of the “juice” consumed in the world. Of course, as Andy notes, “If you’re day drinking, it’s Mint Juleps all around.” But if you’re seeking something else, there are options.
For an elegant experience try the Old Fashioned, made with Old Forester Bourbon, Simple Syrup, Angostura Bitters, and Orange Bitters at The Lobby Bar in The Brown Hotel. Located at 335 West Broadway, The Brown Hotel’s classic Georgian-Revival exterior earned it a spot on the National Register of Historic Places and is easy to spot. The graceful décor offers modern comfort with a fulsome nod to the hotel’s history. Should you not feel like departing after a day at the track, food is available from the English Grill.
If Proof on Main was to your liking for food, or if there’s a wait, have a drink. Sometimes we take minute in the South, so learn to appreciate the time. Wander and chat with a cocktail in your hand. There’s the aforementioned art to explore, but Andy says be sure to check out the one-way glass in the men’s room (I don’t know, that’s what he said, and he’s never steered me wrong). The sheer amount of bourbon available to taste is almost overwhelming, so don’t be afraid to take a departure from the theme. Andy recommends the gin-based Jasmint To Be.
If you can find Hell or High Water, it’s a comfortable little speakeasy just off Whiskey Row. Like any good secret spot, it’s fun to discover. If you find yourself in gift shop about the size of a tight parking spot - you’re there. If half the fun is in the finding, the rest is in the drinking. Hell or High Water offers a host of creative cocktails and mocktails, but the Mischief in Milan was of most interest to me.
Eventually, the track will call. For early risers, head out for Dawn at the Downs and see the horses take to the track for morning work. Gates open at 7 A.M. so the earlier your arrival, the better. Maybe you will see something that tips you towards more informed betting. At some point, even a non-gambler like I am will hear the call of the window. It’s just part of the experience.
Most betting in America is pari-mutuel wagering, in which you’re not betting against the house, you’re betting against everyone around you. So, take a look around. You’re hoping to go home with their money. None of them care how much you bet, but they absolutely care how you bet. I learned from Andy at Keeneland, there are few faux pas worse than arriving at the window to place a bet and sounding as if you’re doing your taxes. So, if you’re a total novice like me, write down your bet, rehearse it, and say it to the teller - slowly and confidently in this order: the amount you are betting, the position of the horse (win, place, or show), and the number of the horse. It sounds like, “$10, Win on the 3.”
There are countless ways to bet, an Exacta, picking the order of the first 2 finishers or a Trifecta, picking the order of the first 3 finishers. Then there are Daily Doubles, a Pick 6, Trifecta Boxes, Dime Supers, Exacta Part Wheels. The variety leaves my head spinning like I just finished a bourbon tour. So, start with the basics - pick a winner. You won’t have Andy to hold your hand as I did, but fortunately the Kentucky Derby offers a primer.
So, we’ve filled two minutes at the track and likely three or four evening hours. There are still approximately 2,358 minutes to fill. Fortunately, Louisville is a great place to wander. Literally. At the Big Four Bridge, a railroad bridge dating to 1895, now reserved for pedestrians on a stroll, you can walk off (some of) the effects of world class food and drink. An average of 1.5 million folks cross the Big Four to Indiana annually. Many of them stop to watch the sunset, then bask in the rainbow of LED lighting. If the bridge didn’t offer a sufficient perambulation, wander Whiskey Row - on your own or with a tour. Taste the work of distillers like Angels Envy, Evan Williams, and Old Forester. Andy’s favorite is the column still at Old Forester.
However you do it, the energy of the Kentucky Derby is undeniable. Amongst the finery of derby hats, the oak and smoke of bourbon, and the beauty of animals surging towards their purpose with a world class athlete astride, fortunes are made and lost. Go, open yourself to the fullness of a classic American experience. Tell ‘em Andy sent you.