Gadling

When the world descends on Louisville for the Kentucky Derby the first weekend in May, those breathtaking thoroughbreds may be first on visitors’ minds, but you can bet bourbon is a close second. Bourbon’s legacy is intertwined with Louisville’s history going back even further than the Derby.

Pioneers in 18th-century Virginia’s Kentucky County found a source of liquid income farming on the 60 acres Thomas Jefferson granted them for raising native corn – they distilled their surplus corn into whiskey. With the local limestone-filtered water and the hardwood trees for barrels, the settlers put their whiskey-making knowledge to work. No matter that the land didn’t suit plowing or traditional rye – they hand-planted and raised indigenous corn. By the late 1700s this area had become part of Kentucky, and thanks to help from the French during the Revolution, one of the counties – one with a great number of the corn whiskey distilleries – was named Bourbon county (today it’s a dry county – go figure).

After the steamboat’s arrival in the Ohio River port town of Louisville in 1811, bourbon found new markets, particularly downriver in New Orleans. Much of the bourbon was shipped out of the original Bourbon county, and some say the Frenchmen reloading the barrels at the Falls of the Ohio (everything had to be unloaded and carried back to the ship on the other side) naturally preferred the name Bourbon.

So what exactly is bourbon, anyway? You may have heard this but it bears repeating. All bourbon is whiskey, but not all whiskey is bourbon. There are some specific requirements about proof, but the gist of it is this: Bourbon is made of more than half corn (at least 51%, though usually much more, among the rye, wheat and barley also used) and it must be aged in new charred-oak barrels. The best way to learn about bourbon, of course is to taste it, and the more open you are to learning from the local bartenders, the more they’ll be happy to impart. Just don’t confuse Jack Daniels Tennessee whiskey with bourbon and you’ll get along fine.Louisville owes its bourbon dominance to Prohibition: Out of the six permits issued in the country during Prohibition to sell whiskey for “medicinal purposes,” four were in Louisville. Still today a third of Kentucky bourbon is distilled in city limits. And a new education and training center andartisan distillery opening this month downtown, the Distilled Spirits Epicenter, will offer hands-on distilling instruction, classes and bottling servicesto small bottlers and those who want to be. Moonshine University, in particular, promises to be fun for enthusiasts.

More importantly to most visitors, though, Louisville is the center of the universe fortastingbourbon. Whether you’re still recovering from college shots or are a whiskey connoisseur, Louisville’s bourbon scene is as multi-faceted as the spirit itself. A day on the Urban Bourbon Trailcan introduce you to the Louisville beyond the cloying mint juleps and floppy hats of Derby.

First, be smart. Especially if you’re not used to it, bourbon sneaks up on you if you imbibe too fast, don’t drink enough water, or consume on an empty stomach. Stay hydrated, eat at every stop, and seriously, take taxis!

Your day starts at Dish on Market, housed in Louisville’s first color motion picture theater. Marshall, one of the two brothers who own the place, loves to talk history. Ask him to tell you about the building and talk bourbon. Meanwhile, order the Presidential breakfast, inspired by Harry Truman’s purported daily meal of toast, eggs, bacon, fruit, milk, and a shot of whiskey, in this case a generous pour of Old Grandad. “This is not your grandma’s bourbon,” laughs Marshall. You may feel like people are staring as your whiskey fumes waft about. That’s OK. They’re just too chicken to go hardcore this early. But like Marshall’s family motto says, you can’t drink all day if you don’t start in the morning. The key is to eat your breakfast first so you have a cushion for your bourbon.

Consider exploring the shops of NuLu (go east on Market) before lunch at Avalonon Bardstown Road, where you’ll want to wander later to check out the fun and funky shops. Like every stop on the trail, folks here know their stuff. If you like drama you might opt for the Flaming Pyroses, a Four Roses Manhattan set on fire (with Grand Marnier – “no bourbon was harmed in the making of this drink,” says Ryan, the bartender). For a less potent option, go for the Kentucky Mule, a twist on the classic bourbon and ginger, and familiar to fans of the vodka-based Moscow Mule. A range of lunch options well below $10 leaves you plenty to spend on drinks if you want to spring for the George T. Stagg, a $30 pour of liquid fire that will singe your lashes as you inhale, but burns oh so smoothly.

If it’s not madness at the track (that is, if you’re visiting outside of Derby week), hit the Derby Cafe in the afternoon to study up on your bourbon, and if you must have a mint julep, kick back at the bar.

After a rest, head for the old-fashioned opulence of The Brown Hotel. Piano music in the lobby bar will set the tone for your genteel sipping. Since this is your first evening stop, ease your way in with a Kentucky Cider – the light Basil Hayden joins sparkling apple cider and lemon for a lovely aperitif. Order a small plate or two – a recent option showcased country ham on brioche with a crayfish salsa, the perfect bite to whet your appetite.

A few blocks, and light years away, next up is the bar at Proof on Main. The restaurant for 21C Museum Hotel, repeatedly ranked among the top 10 hotels in the world, this is your “see and be seen” hotspot stop. Craft cocktails are offered with a selection of heartbreakingly delectable snacks. Don’t miss the cured meats plate, lonzino, lardo, and smoked grapes. The bar menu changes seasonally, but you could ask nicely for a Gold Rush for an all-too-easy-to-down honey, lemon and bourbon drink. Sip among the well-heeled crowd, then take a spin around the confrontingly contemporary art collection.

If you’ve paced yourself, you’re ready for dinner. You’re off to Baxter Station, where you’re unlikely to bump into tourists. Instead, this joint serves comfort fare to a regular crowd of its Irish Hill neighbors, families, white-haired long-timers and a sprinkling of hipsters. Traces of its past remain – once a saloon popular with nearby train station employees (no women allowed in those days), then a grocery during Prohibition, and back to a tavern until a rave restaurant review of the food turned it into a restaurant. Leftover door signage to the twinkly-lit back room remains because they don’t see any need to scratch away the past. This is pretense-free food and drink, no craft cocktails or fusion fuss here. The bourbon fried chicken, hot and crispy as nature intended, will fill you up nicely. Try Old Fashioned with Woodford (invented in Louisville) or choose your bourbon neat from the bar-tab friendly list.

Wrap up your night with dessert at Bourbons Bistro, a mecca for bourbon-lovers with more than 130 selections. Grab a chair at the bar for serious discussion. Tell the bartender what you like – caramel and vanilla, for instance – and he’ll give you a knowledgeable recommendation, like Vintage 17 Year. If you’re not up to straight bourbon, order the Bourbon Cobbler. Dessert in a glass, this sweet cocktail will go down so easily you might find yourself at the bottom tempted to order the 1969 Old Crow, a rare bourbon in a ceramic chess piece – you’ll see the face scowling as he keeps watch over the bar – that costs a cool $125. You might actually see someone order it, and watching a patron sip a drink that spendy is entertainment in and of itself. To finish the night, have the bread pudding. The towering carb-fest not only tastes amazing, but soaks up all that bourbon. You’ll need it – tomorrow is another day in Louisville.

Dana McMahanis a Louisville-based travel, food and fitness writer. Her articles have appeared in Delta Sky magazine, Fodors.com, TheDailyMeal.com, the Huffington Post, and the Pittsburgh Post-Gazette, among other outlets. She blogs here.