The Kentucky Derby Is More Than a Horse Race, It's an Entire Long Weekend

The Derby is slated for Saturday, May 6. It’s among the most exciting moments in sports, but Louisville offers four days of fun surrounding the big race. (Photo courtesy of Louisville Tourism)

The Kentucky Derby Is More Than a Horse Race, It's an Entire Long Weekend

April 24, 2023 –––––– Larry Olmsted, , , ,

Since 1875, the first Saturday in May has been reserved for one of the world’s premier bucket list events, the Kentucky Derby. But while it is famously known as the “most exciting two minutes in sports,” the surrounding party stretches across the entire weekend, with plenty of pomp and circumstance, fancy dress, special events, and food and drink, both inside and outside Louisville’s Churchill Downs racetrack.

“The Derby lasts far longer than two minutes, and the city becomes a hive of activity,” said Brian Ruede, COO of Quint Events, which runs Derby Experiences, the official hospitality and ticket package provider for Churchill Downs and ticketed weekend events. “During the week leading up to the race, Louisville lights up with festivals, parades, sporting contests, and shows.”

Many locals attend every year and have the complex logistics dialed in, including renewable seat licenses that take many of the best seats out of play. But with as many as 170,000 attendees, it can be overwhelming for newcomers to secure hotel rooms and tickets to the race. Making the most of Derby weekend requires a little insider knowledge.

Day Zero

It’s ideal to arrive by Thursday night, if possible, since things kick-off bright and early the next morning.

No event draws more outsiders to Louisville and its small airport, so getting there is the first challenge. Flights into Indianapolis and Cincinnati are much more plentiful and less expensive. Both are an easy drive of less than two hours, while Nashville is an hour further. Another smaller in-state option is Lexington, just 45 minutes away.

All downtown hotels, and most in the surrounding area, sell out far in advance, so book as early as possible. Many run shuttles to and from the track for race weekend, but otherwise your best bet is a rideshare service or public transportation buses (TARC). For whiskey lovers, there are several notable lodging choices, the newest being Hotel Distil in the heart of Whiskey Row, steps from the visitor centers of Rabbit Hole, Angels Envy, Michter’s, Evan Williams, Kentucky Peerless, and Old Forester. A few short blocks away is the large Omni. Its multiple dining and drinking options include the speakeasy-style Pin & Proof, using local whiskeys in its signature cocktails—and a four-lane bowling alley. The Seelbach Hilton, believed to be F. Scott Fitzgerald’s inspiration for “The Great Gatsby,” is among the city’s most luxurious. Its Old Seel-bach Bar is an old school, mahogany-heavy classic with a lengthy list of bourbons. The very first property in the 21c Museum Hotel chain is here as well, and its small size makes rooms hard to get for Derby weekend, but its Proof on Main is worth a visit, with its list of hundreds of whiskeys including nearly three dozen private cask bottlings.

A classic, The Brown Hotel offers a Derby weekend package. Its Lobby Bar has an extensive whisky menu complete with cocktails and a plethora of flights.


The hotel most associated with the Derby is the Galt House, which has two distinct whiskey-centric watering holes: the Jockey Silks Bourbon Bar, with 100 offerings, one of the city’s first such specialists, since 1972, and Down One Bourbon Bar, with 120-plus whiskey choices. The Galt offers special race weekend packages with lots of extras, including on-site parties, but not tickets to the race itself.

The pricier but by far most convenient option is a turnkey package with tickets, lodging, and options for in-venue VIP hospitality lounges and all of the major Louisville events. To keep prices down, Derby Experiences offers lodging options such as Courtyard, Springhill Suites, and Fairfield Inn. These packages include VIP fast-access entry gates into the track, and all packages include ground transportation to and from the races, an invaluable extra.

Dressed up for race day ANDREW KUNG / THE SOUTHERN GLOSS

Thursday night features one of the coolest extracurricular events surrounding the races, Taste of the Derby. Each year star chefs are chosen to represent a slate of high-profile racetracks from the areas around Belmont, Oaklawn, Keeneland, Aqueduct, Santa Anita, and of course, Churchill Downs. These luminaries cook a gala charity dinner, supporting food banks and hunger relief, with tasting stations, wine pairings, and open bar at the KFC Yum! Center sports arena downtown.

Watch Hill Proper KARLA GREEN

Pin & Proof at Omni Louisville MARK O'TYSON

Alternately, Fourth Street Live! is a pedestrianized outdoor entertainment, dining, and retail area in the heart of downtown that notably hosts a free outdoor concert series on Thursday, Friday, and Saturday nights of this special weekend.

Down One Bourbon Bar at Galt House KRIECH-HIGDON PHOTOGRAPHY

Day One

The big deal today is Kentucky Oaks, always on the Friday of Derby weekend. It’s the biggest fillies-only race, and among the most important days in American horse racing. Many visitors don’t realize that all reserved seats for Saturday include Friday as well, so you’ve already paid for it, and that means double the fun, double the hats, double the fancy dress, double the chances to bet, and double the racing action. The Oaks is a fundraiser for cancer charities, so traditionally everyone wears something pink, from ties to dresses, with the same Derby-level of fancy dress. Just as the Mint Julep is the traditional Derby Day drink, the Lily—vodka, orange liqueur, and lemon and cranberry juices—is the official drink of the Oaks, though both are widely sold all weekend. Your seats for both will be the same, so the Oaks is a trial run to get the lay of the land—where you want to watch, what to eat, the closest bar, etc. Like Derby Day, the first race is at 10:30 a.m., and the main event is not until early evening.

If you booked your ticket package through Derby Experiences, you have the option to attend the Fillies & Lillies ball tonight at the racetrack. Held inside the Kentucky Derby Museum, it’s the hottest bash in town and includes live music, dancing, a gourmet Southern buffet by Food Network star Darnell “Superchef” Ferguson, and open bar with specialty cocktails.

The biggest of the many society galas surrounding this weekend is the black-tie Barnstable Brown Gala, hosted at a suburban mansion for over 30 years. It’s the choice of many celebrities in town for the race. Admission is available through several after-market ticket vendors, but prices average close to $3,000 a head.

Alternatively, you can hit the free Fourth Street Live! concerts, the whiskey bar in your hotel, or suburban Watch Hill Proper, which claims to be nothing less than the world’s largest American whiskey bar. With library shelving, leather couches, and deep plush chairs, it has a living room vibe, and even the waiting room has a full bar. It’s a domestic whiskey lounge and they serve nothing else except wine—“nothing clear, nothing foreign, nothing beer.” The list represents 38 states and features 1,648 bottles, including 1,221 bourbons and 1,128 from Kentucky. There are 377 single barrels, 91 of which are bottled in bond, 66 are over 130 proof, and there are 355 1.5-ounce pours under $10, 61 over $100, and all are offered as half-pour options.

Day Two

Morning Fork is a beloved downtown breakfast spot that serves Sunday brunch Wednesday through Sunday, with specialties like Short Rib Benedict and Southern Biscuits and Gravy. They also offer takeout, which is easier at such a crowded time. Just outside the track, horse industry insiders choose to dine at Wagner’s Pharmacy, since 1922.

It’s Derby Day and gates open at 9 a.m., with the first race kicking off around 10:30. There are usually 14 races that day, and all are marquee events, with the big one usually being the twelfth race at around 6:45 p.m. Anything goes in the infield, but in the grandstand, men are expected to wear a jacket and tie, women dress to the nines (but high heels are discouraged!), and everyone dons hats. You cannot dress too fancy on Derby Day.

The lottery for pre-sale tickets from Churchill Downs ends in the fall of the year before the races, so it’s too late for 2023. Ticket brokers like StubHub also sell race tickets, though at inflated prices. Derby Experiences ticket packages are the easiest way to get always sold-out reserved seats, plus lots of extras and options including seats in premier lounges with food, entertainment, and open bar. However you obtain tickets, make sure to look for covered seats, since it usually is either hot or rainy. The lower cost or last-minute approach is general admission, standing room tickets to the track infield which never sell out but are far less comfortable and far more weather affected, with fewer amenities available and more of a spring break vibe. You may bring folding chairs or picnic blankets to the infield. Two-day tickets go on sale the previous November, rising three-fold in price as the race gets closer, but typically run close to $200. You can also buy one-day infield tickets to the Oaks or Derby at the gate.

Food can be brought into Churchill Downs only on this weekend, and many regulars who choose the infield bring their own food (no outside alcohol allowed). Louisville’s most traditional boxed-lunch providers are Wiltshire Pantry, The Cheddar Box Café, Stevens & Stevens Delicatessen, and Morris’ Deli Liquor& Catering. But there is plenty on offer at the infield and grandstand concessions, and Derby Day standards include pulled pork sandwiches, pork rinds with pimiento cheese, and the Kentucky specialty burgoo, a meat stew with lima beans and other veggies.

Watch Hill Proper

For nearly a century, the Mint Julep has been the official drink of the Derby, but while Woodford Reserve is the race’s longtime official bourbon, the drinks served at most track venues are premade Old Forester ready-to-drink cocktails. Tradition dictates the cocktail be served in a silver cup, and that’s what many bars around town use. But since 1939, the Juleps at the track have been served in an annual special-edition souvenir glass with the name of every winner on it. For regulars, these keepsakes have become collectibles, with some collections going back decades, so make sure to take yours home.


Churchill Downs Racetrack 700 Central Ave.;


Fourth Street Live! 411 S. Fourth St.;


Taste of the


Cheddar Box Café 1211 Shelbyville Rd.;

Morning Fork 1722 Frankfort Ave.;

Morris’ Deli Liquor & Catering 2228 Taylorsville Rd.;

Stevens & Stevens Delicatessen 1114 Bardstown Rd.;

Watch Hill Proper 11201 River Beauty Loop, Prospect;

Wagner’s Pharmacy 3113 S. Fourth St.;

Wiltshire Pantry 901 Barret Ave.;


21c Museum Hotel 700 W. Main St.;

The Brown Hotel 334 W. Broadway;

Galt House 140 N. Fourth St.;

Hotel Distil 101 West Main St.;

Omni Louisville 400 S. Second St.;

Seelbach Hilton 500 S. Fourth St.;