A Few Days In

An Easy-to-Follow Kentucky Derby Weekend Guide

by Nicole Kliest
Kentucky Photo by Gene Devine/Unsplash.

LOUISVILLE, Kentucky — In 1875, 10,000 spectators gathered around fifteen horses in a field called Churchill Downs in Louisville, Kentucky. It was May 17, and after a riveting one-and-a-half mile race, Aristides reigned victorious.

Fast forward to present day, and things have more or less remained the same.

If you get sentimental about tradition and have booked a seat to witness the Kentucky Derby — a.k.a. the most exciting two minutes in sports — you’ll need something to do to fill the rest of your time in Louisville. (Ahem, bourbon.)

It turns out this part of Kentucky is home to a slew of historic hotels, buzzworthy restaurants and bars, and nature-minded activities like horseback riding and farm tours. Even a quick weekend trip here leaves you with a strong sense of place. Why? Because Kentucky is unlike anywhere else in the United States. Consider this an easy-to-follow guide on where to stay, what to do, and the best places to eat and drink in Derby City.

Photo courtesy of 21C Museum Hotel.
Photo courtesy of The Grady.
Photo courtesy of The Brown Hotel.

Where to Stay

An Art-Filled Hotel
It’s a hotel! No, it’s a museum! Wait, it’s both! The 21c Louisville in downtown is a boutique hotel that doubles as a contemporary art museum — the first of its kind. Housed in a former 19th-century warehouse, you'll find more than 9,000 square-feet of exhibition space to discover. The hotel rooms pay homage to the building's historic roots. with exposed brick walls, high ceilings, and large windows. Read more about 21c on Fathom

Historic Digs
Another option is The Grady, which is housed in the former apothecary where pharmacist J.B. Wilder produced medicinal bourbon bitters and elixirs in 1883. Take in the original reclaimed wood ceilings and historical artwork while you sit by the dramatic lobby fireplace.

You’d be remiss to forget about The Brown Hotel, another Louisville property with historic roots. The building — recognizable for its Georgian-Revival façade — is listed on the National Register of Historic Places. If you’re into that whole "it’s like stepping back in time" thing, you'll find your home here.

Left: Churchill Downs; Right: Kentucky Derby Museum.
Hat making at Formé Milinery. Photos by Nicole Kliest.
Left: Woodford Reserve; right: Old Forester. Photos by Nicole Kliest.
A thoroughbred at Old Friends. Photo by Nicole Kleist.

What to Do

Visit the Racetrack
Churchill Downs is where the magic happens on race day. No matter when you're heading to Louisville, it's with visiting the Kentucky Derby Museum to dive into the history and cultural context of America’s longest continually held sporting event. One of their permanent exhibits, Black Heritage in Racing, examines the Black horsemen from the early days of racing, like Oliver Lewis, the first jockey to win the Kentucky Derby back in 1875 while riding Aristides, a horse trained by another Black horseman, Ansel Williamson.

Explore the Kentucky Bourbon Trail
It would be sacrilegious to travel to Louisville and not pay homage at one of the many iconic stops along the Kentucky Bourbon Trail. Two ideas to get you started: Woodford Reserve, which also happens to be the official sponsor for the Derby (we love a full circle moment) and Old Forester Distillery. A tour of both of these larger-than-life distilleries gives you a behind-the-scenes look at the process of how your favorite bourbons and whiskies are produced.

Shop For a Derby Hat
Among the more celebratory traditions that comes with attending the Kentucky Derby, showing off a flashy hat ranks high on the list. If you’re still without a topper, stroll over to Formé Millinery Co. on East Main Street for a handcrafted accessory made by owner Jenny Pfanenstiel. If you’re feeling especially spendy, splurge on one of her Woodford Reserve Derby Collection pieces.

Interact With Thoroughbreds
There are more than 200-plus retiree thoroughbreds at Old Friends — from Kentucky Derby winners to horses who never started a race. Founded by Michael Blowen, this unique living history museum should be on every Louisville itinerary, especially if you love interacting with horses. If you’re feeling inspired after visiting to the farm, consider participating in Woodford Reserve’s $1,000 Mint Julep Cup. Every year, the distillery runs a charity program for Derby that sells $1,000 mint julep, with all proceeds going to their charity of choice (this year's it's Old Friends).

Barn8 at Hermitage Farms. Photos by Nicole Kliest.

Where to Eat and Drink

Farm-Fueled Meals
For a Caesar salad that one insider told us is “basically crack,” head to Bar Vetti. If you’re looking for a tasting menu that will exceed expectations, chef Edward Lee's 610 Magnolia in the heart of Old Louisville is a must. Feast on dishes like tai snapper with kinilaw, coconut, red onion, and finger lime, followed up by snow crab with Korean steamed egg and black maitake, and finished off with pork loin belly served with red beans and Jefferson red rice and blistered shishitos. (The seasonal menu varies from week to week.) If you’re looking for a rustic vibe, Barn8 at Hermitage Farms is the ultimate choice. The restaurant located on the grounds of historic Hermitage Farm serves a delicious menu of farm-to-table bites. The smoked trout dip is to die for.

Classic-Meets-Contemporary Cocktails
Because Louisville is the land of bourbon, you’ll want to add some beverage stops to your itinerary. Pendennis Club — where the Old Fashioned is said to have been invented — is a member’s club founded in the 19th century. If you know (or can meet) a member, go. If you’re leaning toward a less formal setting, grab a drink at Expo, a cocktail bar with no outdoor sign and a killer beverage program.

Keep Exploring Kentucky

More Than a Derby Town, Louisville Is a Movable Feast
Bourbon for Breakfast. Playing the Ponies at Lunch. Fried Chicken for the Plane Ride Home
Royal Ascot: Big Day at the Races