Seeking out the best of Kentucky behind the Holy City's bars 

The Bourbon Trail

Polishing off a handle of Rebel Yell over a weekend may mean you're an accomplished bourbon drinker, but it doesn't mean you know a thing about bourbon. Although "bourbon and ginger" is perhaps the most frequently ordered cocktail in Charleston, the corn-syruped, low-grade house concoction has blinded many to the not-so-subtle variances that make a fine, handcrafted bourbon truly memorable.

Many bourbon drinkers scoff at the notion of pouring a small-batch whiskey with a cocktail, but as a few of the drinks we discovered attest to, a perfect cocktail requires the perfect liquor. Still, a few bourbons require, and even demand, a lack of accompaniment. It is in these complex tastes that we truly discover the essence of an American spirit.

Blanton's
Served on the rocks
Club Habana

No sensation can duplicate the combined essence of a fine bourbon and a good cigar. With layers of complexity — orange, smoke, vanilla — Blanton's is perhaps the most flavorful bourbon available. It's also the first single barrel bourbon ever produced, and the most popular for cigar pairings at Club Habana. "It's definitely our favorite here," says operating partner Justin Valakis. "Blanton's really pulls the flavor out of a medium-bodied cigar." Valakis recommends the Winston Churchill Marrakesh with Blanton's, a creamy, citrusy cigar from the Dominican Republic.

"Blanton's has lots of flavors, and is already smoky, so you want to go with something that can carry that, so you're not just getting smoke and smoke," he says. "Together, you've got the citrus and orange of Blanton's playing off the cream and nut of the cigar, while the caramel and vanilla of the bourbon play off the wood and spice of the Churchill. The rule of thumb is not so much to play opposites, but to give one or the other the power to extract flavors."

Like grapes in wine, cigars draw their flavor from the soils they're grown in. Enjoyed with Blanton's, the combination of Caribbean smoke and Kentucky spirit merge and erupt into an unparalleled explosion of pleasant flavors.

The Marque Manhattan
2 oz. Basil Hayden Bourbon 3/4 oz. Punt e Mes Vermouth Bing cherry infused with brandy
Blossom

Few fine bourbon distillers recommend mixing their product with anything, but Basil Hayden's makers actually suggest adding a bit of ginger ale or soda water. With its especially sweet taste and light finish, Blossom bar manager Brian Solari settled on Basil Hayden (aged 8 years; 80 proof) for the restaurant's signature cocktail, the Marque Manhattan.

Served in a martini glass, the bourbon's brisk flavor cuts through its sweet companion, Punt e Mes vermouth. But the simple cocktail's lasting charm lies in the final sips, when the brandy-drenched flavor of a whole Bing cherry (think full cherry texture — no maraschinos here) envelops the palate.

"We soak them for three months," says Solari. "I wouldn't let anybody taste them when we introduced the drink, or they'd have been gone."

1792 Ridgemont Reserve
(with Seared Scallops) Served straight, in a neat glass
Thoroughbred Club

Mouzon Taylor is a man who knows his bourbons. The Thoroughbred Club is perhaps the one bar in town where orders for dark liquors outweigh the lights, and Taylor's been recommending bourbons and pairings at the Charleston Place bar for over 12 years. His favorite bourbon, 1792 Ridgemont Reserve, was featured in a pairings dinner he hosted in November, matched with a plate of two giant seared scallops over sautéed mushrooms, all under a rainbow of bacon.

"The scallops have a lot of seasoning and pepper flavor, so their spiciness pairs well with the 1792," says Taylor. Because its recipe favors rye over barley and wheat, 1792 first hits the palate with a poignant nutmeg and allspice flavor, before finishing with a nectarous zest. Served room temperature in a wide-based "neat glass," the aromas come on strong, and none of the flavor is diluted.

A true whiskey connoisseur, Taylor's skill at pairing foods and bourbon is stunning. "I appreciate bourbon and single malt scotches so much," says Taylor. "I wanted to figure out what I could do with them and eat at the same time."

Baker's Bourbon
With Braised Pork Belly

Baker's Seven-Year Bourbon
Served in a 2 oz. snifter
Blu Restaurant

At 107-proof, Baker's Bourbon bursts onto the palate, delivering strong notes of vanilla and a sharp, fruity finish. At Blu Restaurant, Chef Jonathan Hagins knows how to counter and complement a bourbon's intensity.

Since the restaurant's opening last March, he's hosted two bourbon dinners. The last featured the Beam family of small-batch bourbons — Booker's, Baker's, Basil Hayden, and Knob Creek. At our tasting, he braises a Kurobuta pork belly. Fatty and rich, he tops the meat with a pan-fried quail egg and a housemade reduced-coffee peach barbecue sauce, all over a bed of Anson Mills grits.

Each bite, followed by a splash of Baker's, is a phenomenal array of coffee, vanilla, and salty, perfectly-textured pork.

"It's just like bacon, eggs, and coffee," Hagins says.

The Old Fashioned
1.5 oz. Woodford Reserve Bourbon Orange slice 2 cherries Dash of simple syrup Splash of sweet vermouth 4 shakes Fee Brothers bitters Soda water to finish
Social

Two weeks after moving to Charleston, bartender Jon Calo met a gruff, burly Southern man named Carriage John. The carriage tour operator ordered Woodford Reserve in an Old Fashioned, one of the first and most enduring cocktails.

With hints of cherry drawn from the oak barrels in which it ages, Woodford's sweet complexion favors its inclusion in drinks like the Old Fashioned. Calo begins by muddling orange, cherries, and housemade simple syrup in a glass. Woodford and a splash of vermouth are added, before the crucial ingredient, bitters, a pungent component of most of the cocktails of the early 20th century. After four generous shakes, Calo adds ice and tumbles the drink, then tops it off with soda water.

The result is a classic cocktail with a palatable depth and multi-dimensional intrigue. Carriage John still visits Calo at Social, often ordering a dozen of the cocktails to share with friends, and always paying with his signature two-dollar bills.

"People that love them love them," says Calo. "And they won't drink anything else."

Pappy Van Winkle
Served neat, in a Glencairn glass
McCrady's

Pappy Van Winkle 20-year bourbon tastes like the ambrosia of dreams.

"There is no other bourbon," says McCrady's Chef Sean Brock, straight-faced. "Everything else is just brown water." When they can keep them in supply, McCrady's stocks the 10-, 12-, 15-, and 20-year bourbons behind their bar. Aged in American oak, Pappy takes on more of the wood's flavor notes the longer it sits, from caramels to nuttiness to vanilla. At 107-proof, the 15-year engulfs the palate, sending its recipient floating away into bourbon-enlightened heaven. It's Brock's favorite.

"It gets on top of your whole mouth," says the chef. "I like a little more burn, a little more punch. The 15-year has a robust flavor."

While most bourbons are aged six to eight years, Pappy Van Winkle's most affordable liquor is aged 10 years. And even that is too good to mix with anything but a drop (literally, from a coffee stirrer) of water, says Brock. The only garnish is the occasional lemon peel wiped around the rim of a Glencairn glass (designed specifically to accentuate whiskeys) to open up the sides of the tongue.

Having a bottle of 20-year on the shelf is akin to keeping a Porsche in the garage — you might only drive it once a month, but it's a damn good feeling knowing it's there. But after the bottle is open, how do you keep from drinking it? Perhaps just by knowing that when it's gone, you'll have to wait for the tiny distillery to release more. "Once you get on the train and then find out you can't get any, it's like, 'What do you mean I can't get it?'" says Brock. "I want it."

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