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An Insider’s Guide to the Kentucky Derby

Kentucky Derby Race

Photo: Bill Brine

When the fifteen horses comprising the inaugural Kentucky Derby field pounded around the track in 1875, 10,000 spectators looked on from a grandstand that still didn’t have a name. These days, the Kentucky Derby draws a cheering crowd of more than 160,000 and has gone on to become not just a rite of spring but one of the top sporting events in the world.

For XOJET clients, a trip to Churchill Downs couldn’t be easier. Louisville is home to a number of well-positioned airports as well as a terrific transportation system, great hotels, and a mix of time-tested and contemporary restaurants.

Here’s the inside track.

Getting to the Derby

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FBOs at two airports offer easy access to Louisville. SDF (Louisville International/Standiford Field) is just a fifteen-minute drive from downtown; Clark County Regional Airport in Jeffersonville, Indiana is also within 20 minutes of Louisville.

Of sentimental note for aviation enthusiasts, or for those flying in on smaller aircraft, just ten minutes from downtown Louisville is the smaller Bowman Field, which, in addition to being the oldest continuously operated airfield in North America, hosted Charles Lindbergh and the Spirit of St. Louis soon after Lindbergh’s historic transatlantic flight. It’s also the site of Bistro Le Relais, one of Louisville’s most highly rated French restaurants.

Churchill Downs is just five miles outside of downtown Louisville.

What to Watch For

Kentucky Derby Guide


The 20 horses that will compete in the 2017 Kentucky Derby have been chosen based on a point system. Girvin, a Kentucky-bred dark bay trained by Joe Sharp leads with 150 points; Irish bay Thunder Snow and Todd Pletcher-trained Always Dreaming round out the top three with 100 points each. But it’s not just about the points. Although he’s only earned 32 points, Classic Empire, whose sire also fathered Triple Crown winner American Pharoah, is emerging as an early favorite, as is McCracken, who can end a race with a sudden burst of speed.

Where to Stay

The Brown Hotel

The Brown Hotel In Louisville, Kentucky

Photo: Chris Witzke; The Brown Hotel

Since 1923, Louisville’s most elegant downtown address has been The Brown Hotel, a 293-room Georgian-style hotel known as much for its elegant public spaces—the gilded lobby ceiling is a work of art—as it is for welcoming, effortless service. Rooms are decorated with dark woods, ornate fabrics, and tasteful equestrian details. A club lounge offers privacy and makes breakfast easy, but you’ll definitely want to have a mint julep in the buzzing iconic Lobby Bar. Here you can follow bourbon flights with a Hot Brown, an open-faced hot turkey sandwich topped with tomatoes, bacon, and cheesy Mornay sauce that was invented at the hotel.

The Seelbach Hilton

When the Seelbach Hotel opened in 1905, 25,000 people came to take in the hotel’s lavish marble floors, tall Ionic columns, huge Persian carpets, grand staircases, and great expanses of imported wood. Today, many of these original details remain, particularly within the public areas and suites, where the hotel radiates lovely, old-world charisma.

History abounds: Escape hatches and warren of subterranean tunnels were supposedly constructed to allow Al Capone to slip out if necessary, and F. Scott Fitzgerald was not only a regular, but, supposedly, regularly thrown out of the bar.

21c Museum Hotel

Proof on Main at 21c Museum Hotel. Photo by Magnus Lindqvist

Photo: Magnus Lindqvis; Proof on Main at 21c Museum Hotel

It’s all about art at 21c Museum Hotel, which houses a free contemporary art museum in addition to 91 serene rooms done in pale blue, white, and charcoal. Although all the rooms feel spacious and open, the aptly named Balconies are set with large terraces that overlook the city. There’s also a huge one-bedroom apartment and The Cyclone, an immersive art experience created by artists Jonah Freeman and Justin Lowe.

Where to Eat

Jack Fry’s

Jack Fry's. Photo by Anthony Raspberry

Photo: Anthony Raspberry; Jack Fry’s

Established in 1933, Jack Fry’s is as vibrant as ever, serving up shrimp & grits, fried oysters, and gorgeous slabs of beef, pork, and duck in a bustling saloon-style space. There’s live jazz every night, too.

Lilly’s Bistro

With a refined dinner menu that offers everything from black truffle gnocchi, braised lamb meatballs, and coconut fried shrimp to a superfood salad or farmer’s platter, Lilly’s lets you be as extravagant or as virtuous as you choose, without sacrificing flavor.

Pat’s Steak House

It doesn’t get any more old-school than Pat’s, where giant steaks come with a house salad and two sides and appetizers include Irish Stew, sautéed frog’s legs, and shrimp cocktail.

Where to Drink Bourbon

One of 27 rack houses for maturing Jim Beam bourbon whiskey located in Clermont, Kentucky.

Photo: Bbadgett

You can’t go wrong at The Brown Hotel, Seelbach Hilton, and 21c, which are home to bars with deep reserves of Kentucky bourbon (21c’s Proof Bar serves 85 different bourbons) and knowledgeable staff members. The bartenders at Doc Crow’s can pair just the right bourbon with the restaurant’s superior ribs; located in a former underground parking garage, Down One offers a selection of 170 bourbons; Haymarket Whiskey Bar is almost as well known for its nearly 400 whiskeys and 250 unique expressions of bourbon as it is for its pinball machines.

Prefer to go to the source? Make a reservation for in-town bourbon tours and experiences at Evan Williams, Peerless, Angel’s Envy, Bulleit, or Jim Beam. Combined with a weekend at the Derby, you couldn’t possibly find a better way to embrace the spirit of Kentucky.

By Katie McElveen

Travel and lifestyle writer Katie McElveen discovered the joy of wandering when, as a teenager, she made a wrong turn in rural South Carolina on the way to a family vacation and ended up taking back roads nearly all the way to the beach.  Since then, she hasn’t stopped exploring, although she now travels with a map and more than $3.00 in cash. Based in Columbia, South Carolina, Katie has shared her discoveries through her work in magazines such as Real Simple, Business Traveler, Modern Bride, Destination Weddings & Honeymoons, Town & Country, Southern Living, Spa and Tennis.