For two minutes on the first Saturday of May, the city of Louisville, Kentucky, becomes the center of the sporting universe. We’re speaking, of course, of the Kentucky Derby, the longest continually run major sporting event in the United States, when the best three-year-old thoroughbred horses in the world streak around the famed dirt track at Churchill Downs for their shot at immortality.
This year, for the first time since 2019, the race will go off in all its glory as an estimated 170,000 people will fill the track. Known affectionately by city residents as the biggest cocktail party of the year, the race is the official kickoff to the summer social season when tourists flock to a city that Southern Living recently named one of the South’s best cities.
The 148th running, this year’s race has been one that Trey Zoeller, the founder of Jefferson’s Bourbon, has looked forward to all year. A native son who has spent most of his life in Louisville, he has his best suit pressed and is ready to head to the track for a few customary mint juleps.
“The last couple of years have been a version of the Kentucky Derby light, something I had never experienced in my life and never hope to again. It cast a pall over the state,” he tells InsideHook. “The town has been buzzing for weeks now with the anticipation of finally doing the Derby right again. It will be an epic weekend filled with cocktails, brews, laughter and hopefully some winning bets on the horses. A good Derby sets the tone for the summer here, and it should be a memorable one this year.”
But Zoeller will tell you not to fret if you miss the race. Louisville is a city that can offer a memorable time year-round and, no offense to Derby goers, is best visited once the race crowds leave.
“There’s always been a Laissez les bons temps rouler attitude here — we like to let the good times roll. It’s due to traditional drivers of the state’s economy: bourbon, marijuana and gambling on horse racing. We’re rebels at heart,” he says. “That’s why there are so many great places to sip cocktails, eat food and have a fun night out, especially since the bars don’t close in Louisville until 4 a.m. We are the northernmost Southern city, so there is an interesting mix of sophistication and relaxation infused in the city, and the people are genuinely nice.”
For those missing out on the festivities of Derby weekend, we asked Zoeller for the places he personally takes visitors when they come to the Ville, as the locals call it. He didn’t include Kentucky Artisan Distillery, the home of Jefferson’s Bourbon and a 30-minute drive from downtown Louisville, so consider that a bonus stop.
Where to Eat: Tasting Menus to Farm Restaurants
610 Magnolia
“My good buddy Edward Lee, owner and chef, consistently does a great job here. Any time you can get a table, something not that easy, and dive into his tasting menu, you will be rewarded with an inventive meal filled with local items. Plus, his bourbon and wine list are great.”
Jack Fry’s
“This is a Louisville staple that has been around since 1933. It reminds me of Raoul’s in SoHo in New York City. I love sitting at its intimate bar where you can always strike up a good conversation with someone sitting next to you. Their shrimp and grits are out of this world.”
Guacamole
“This new spot in the red-hot neighborhood of Nulu downtown that’s funky and fun with great bars and restaurants. Housed inside a building with a huge mural of Frida Kahlo on the front, you know it will be interesting. I love their fresh takes on classic Mexican dishes, and they have one of the best tequila lists I have seen.”
Barn8 on Hermitage Farm
“Located just outside town on a beautiful horse farm inside an old barn, this place is worth visiting just to enjoy the scenery. It’s amazing. It was opened by the same people who opened the 21c Museum Hotel downtown. The attention to detail is great, and the food is excellent.”
Decca Lounge & Restaurant
“Brunch is a southern staple, and Decca does it better than anyone. Their food is superb and fresh. It is brimming with energy, and I always bump into someone there. Best of all, upstairs is B-Side, a bottle, book and specialty LP store that is just cool.”
Where to Grab a Drink: Cocktail Bars to Breweries
Hell or High Water
“This speakeasy-style cocktail bar is located underneath the Old Forester Distillery right in the heart of the Urban Bourbon Trail. You have to make reservations to get in, and it’s worth it. It’s got a great vibe, killer drinks and is near the great tasting bars for Michter’s and Rabbit Hole distilleries.”
Taj
“Housed in a skinny little bar in Nulu, this place has an incredible bourbon portfolio and good cheap beers. I love hanging in its courtyard out back, especially when they crank up the karaoke at night. It’s the perfect spot for some late-night fun.”
Neat Bourbon Bar and Bottle Shop
“As a bourbon lover, this place has one of the best lists in the city since they buy old bottles from estates using Kentucky’s Vintage Spirits Law, so you are sure to find some wild stuff here. Even better, they can sell you bottles to go.”
3rd Turn Brewing
“I love this brewery housed in an old plant nursery located right by the Kentucky Artisan Distillery where we make our product. Their beers are great, and drinking them in the old greenhouses filled with huge vines and plants on a hot day is perfect.”
F.A.B.D Smokehouse
“A true locals hangout, this old package store always has a smoker going out front upon which they cook some of the best ribs and chicken in the city. The inside is a relaxed combo bar and package shop where everyone hangs out and has fun.”
What to Do: Museums to Parks
Frazier History Museum
“Located downtown, this is the official Kentucky Bourbon Trail Welcome Center. It tells the story of bourbon so well, identifying everyone and everything that has and is involved in making our spirit. There are interactive exhibits, and they sell some rare bottles too, of course. It’s also across from the Louisville Slugger bat museum, something that every Louisville kid visits in their youth. It’s pretty cool watching them make the bats.”
Waverly Hills Sanatorium
“Supposedly, this is one of the most haunted places in the world. It’s a gothic building that exudes such an uncomfortable vibe that I love taking people there for a tour. If that place doesn’t drive you to a drink, nothing will.”
Cherokee Park
“Anyone who grew up in Louisville has spent hours in Cherokee and neighboring Seneca parks. Designed by Frederick Law Olmsted, the same man who created Central Park in New York City, you can easily get lost in its many wandering trails that lead to hidden nooks and crannies. In the summer, everyone seems to head there to hang out on Beargrass Creek.”
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