Food & Drink

How to Make an Old Fashioned Cocktail + Cigar Pairing Recommendation

By John Pullo

The Old Fashioned cocktail…a staple of every “Five Drinks You Must Learn to Make” list, and a storied libation that’s so much more than just a Mad Men prop: it is, by many accounts, the most popular drink in the United States.

It also turns out that AJ Fernandez is quickly becoming one of the top go-to guys for best-in-class Nicaraguan cigars.

And this is what happens when these two great things come together into one: an Old Fashioned cocktail & cigar pairing.

Today, we’re going to show you how to make an Old Fashioned the Famous Way…or more precisely, the way it’s done at Leaf Cigar Bar & Restaurant here in Easton, PA. There are many old fashioned drink recipes; we prefer to use a fine bourbon, whose distillery is a National Historic Landmark: Woodford Reserve. And we’ve paired our Old Fashioned recipe with a new, flavorful smoke from AJ Fernandez that’s called Shadow King. Both the Woodford and the Shadow King are rich in flavor, loaded with subtle nuances, and deceptively smooth: when combined, this combo just may put some hair on ya’ when you’re not looking.

What is in an Old Fashioned?

Excellent question. The original Old Fashioned recipe, as quoted by, was “a potent concoction of spirits, bitters, water and sugar.” There was no specific mention of bourbon or whiskey made, just that you should use “a stimulating liquor” when preparing it – which is why some different Old Fashioned drink recipes called for gin.

But credit where credit is due: the Pendennis Club in Louisville, KY is held in high regard for creating the whiskeyed-up version of the Old Fashioned cocktail. If you told me that whiskey flows from the tap in the Bluegrass State, I might believe you; so a no-brainer here as to why their “stimulating liquor” of choice was Kentucky Straight Bourbon. The Old Fashioned is so entwined with Kentucky’s bourbon culture that it’s been named Louisville’s official drink – there’s even a two-week festival every June to celebrate it. Let’s get started a little early…

Leaf Cigar Bar’s Best Old Fashioned Drink Recipe:

Watch Chad do it behind the bar at Leaf:

How to make an Old Fashioned drink, like we do at Leaf: get yourself a rocks glass. Don’t panic – it’s also called an Old Fashioned glass, so it takes the guesswork out of it for you.

Start with a half packet of sugar (you could go old school and use a sugar cube, but you’re going to muddle the ingredients – so not a deal breaker). Add the cherry, orange wedges and 3 dashes of bitters. Then, splash in the club soda and muddle the whole shmear in the glass. Add the Woodford Reserve, then top it up with a big scoop of ice. Sip and enjoy, with the satisfaction of knowing you made the best Old Fashioned cocktail in town.

Old Fashioned Cocktail Cigar Pairing: Shadow King by AJ Fernandez

Even if I didn’t name-drop AJ Fernandez, you’d expect the Shadow King blend to be a full and enjoyable ride, just based on how it hits your ears: a mix of vigorous Nicaraguan, Honduran, and Dominican long fillers, coupled with a subtly-sweet San Andres binder and finished in a very dark Ecuadorian Sumatra Oscuro wrapper leaf. Smoking it is proof, evidenced by the tasting notes: earth, spice, espresso, cocoa, cedar, leather, citrus and black pepper.

Those play well with the 90-proof Woodford Reserve, whose amber color holds some interesting flavors within: dried fruit, cocoa and tobacco spice are present on the nose, while spice, fruit & floral flavors splash across the taste buds with a long and silky-smooth finish.

How It Smokes

The prelight will have already tipped you off: black coffee, earth and a bitey spice that leaves a tingle on the inside of your cheeks. A good Old Fashioned drink like this makes everything a little less edgy. The Shadow King’s eventual leather, citrus and pepper notes complement the fruit and Woodford Reserve – the other flavors balance the bite.

Great smoke output, long burn, and designed to satisfy the needs of those who like their cigars medium-full and up.

A dark, full-flavored stunner, Shadow King stands up to the Old Fashioned quite nicely; that alone makes this AJ Fernandez smoke worth a try. And now that you’re well-versed in how to make an Old Fashioned, it’s up to you to see for yourself. Cheers!