It's only about a five-hour drive from Chicago to Bourbon Country, where an array of distilleries dot the landscape around Louisville. The distilleries are fun, of course, but sampling bourbon isn't the only reason to head to Louisville—the city also has numerous restaurants and bars worth the drive, too. Here's an itinerary for a food- and booze-filled Kentucky weekend, from excellent Bloody Marys to tacos.
RECOMMENDED: Weekend getaways from Chicago
Breakfast & brunch
Atlantic No. 5
Located along Main Street, Atlantic No. 5 offers sandwiches and salads for lunch and early dinners (it closes at 6pm). It's also open for breakfast, when an egg sandwich or frittata will only set you back $5 or $6, and the cold brew or latte is exactly what you need if you had too much bourbon the night before.
St. Charles Exchange
If your brunch requirements include great drinks, head to St. Charles Exchange, where you can choose from several Bloody Marys, including a smoky tequila version. The whole drink list is available, so try some others, too. Bartenders around the country contributed drinks, like the Shadow Puppet #2, a mix of rum, genever and apricot. For food, you won't go wrong with anything, but pork belly hash and fried chicken and biscuits will help soak up the cocktails.
The Brown Hotel
The Brown Hotel is a gorgeous hotel from the 1920s that was renovated and reopened in the '80s. Located downtown, it's a convenient spot to stay if you're exploring the rest of the city, and it's also a good spot for lunch. The hotel is the originator of the Hot Brown, an open-face turkey sandwich that's topped with bacon and Mornay sauce. It's available at all three dining venues within the hotel.
For a casual dinner, the honky tonk–themed Silver Dollar serves up seasonal dishes, plus brisket, ribs, and a few chilis. There's a huge whiskey list, but you'll find a variety of spirits represented on a list of well-made cocktails, which cost $9 each. Bonus Chicago connection: Beverage director Susie Hoyt used to work at the Violet Hour. She also works at El Camino, where you'll be going for tiki later in the evening.
Rye on Market
Rye melds a range of influences into its cuisine—think kimchi waffles, grits and succotash, and corn ravioli—but uses local ingredients. There's an abundance of meats and cheeses and seasonal vegetables, and local fruits make their way into cocktails and desserts. The menu encourages sharing, but we ran into trouble with our large group: The food is so good, you'll have a hard time sharing it with the rest of the table.
If Big Star and Three Dots and a Dash had a love child, you'd want to go there immediately, right? That's El Camino, a taco and tiki spot that also has firepits outside. There's a perfect daiquiri, as well as a terrific Mexican Firing Squad, plus tacos and tortas to snack on.
Willett makes some of my favorite bourbons, and you can see how they're made by taking a tour of the distillery (tours are 10am–4pm on the hour Monday–Saturday and 12:30–3:30pm on the hour Sundays from March–December). Located about a 45-minute drive from downtown Louisville, Willett makes a variety of bourbons, including Johnny Drum, Rowan's Creek and the Willett line, and you can see the process, then taste a couple offerings.
Heaven Hill Distillery
It's kind of cool to contrast a smaller distillery like Willett with a behemoth like Heaven Hill. And it's a short drive between the two, so it's easy to do both in an afternoon. At Heaven Hill, there's the Bourbon Heritage Center, which is basically a bourbon museum, plus rickhouses (where barrels of bourbon age) as far as your eyes can see. Walk around a few of those, plus sample bourbons like Evan Williams and Elijah Craig on a tour. There are three levels of tours offered, each multiple times a week.