• Captain Corey

The Old Fashioned... History & Variations

From the local pubs to the high scale dining establishments, and every place in between, the Old Fashioned cocktail is most likely one of the highest demand "involved" libations on the menu, or off of it. However, the variations can differ from place to place. To understand this a bit better, let's first get an understanding of the history of this "Old Timer".

To do so, we'll need to travel back to the Waldorf-Astoria Hotel bar in 1880. This is where the birth of the Old Fashioned took place, although, the cocktail is said to have been conceived in Louisville, KY. The gentleman credited with it's introduction to the world is Colonel James E. Pepper(1850-1906). Col. Pepper was a horseman of international fame, operating the "finest stable in Kentucky", with his thoroughbreds competing across America and Europe. Also a "Bourbon-Industrialist", as a third generation producer of "Old Pepper Whiskey", Col. Pepper traveled the country in luxury, aboard his private rail car named "The Old Pepper".

These travels often brought him to New York, and more specifically, to the Waldorf-Astoria Hotel bar. While there, he was regularly seen socializing with the likes of other famous captains of industry, including John D. Rockefeller, Theodore Roosevelt, C.V. Vanderbilt, Charles A. Pillsbury, Fred Pabst, Charles L. Tiffany, & William Steinway. It was in the company of these elite gentlemen that Col. Pepper introduced the world to the Old Fashioned cocktail. However, legend has it that the concoction was invented in his honor by a bartender at the famed Pendennis Club in Louisville.

Jump back a few years, to 1806, where the first recorded definition of the term "cocktail" reads, "a stimulating liquor, composed of spirits of any kind, sugar, water and bitters". So, the foundation for what would become commonly known as the Old Fashioned was already in place by the time that that unnamed bartender at the Pendennis Club concocted the special mix for Col. Pepper. It only makes complete sense that whiskey would be the spirit chosen to honor him. Here's how that original recipe might have looked...

"Dissolve a small lump of sugar with a little water in a whiskey-glass; add two dashes Angostura bitters, a small piece of ice, a piece of lemon-peel, one jigger whiskey. Mix with small bar-spoon and serve, leaving spoon in glass." (Modern American Drinks by George Kappeler, published in 1895)

Through my research for this post, I've discovered a few things about the Old Fashioned, that may slightly alter my future preparations of the cocktail. For instance, what about the cherry and the orange? Mr. Boston Official Bartender’s Guide: 75th Anniversary Edition, although open-minded about [muddling] the orange, approves of the cherry only as a garnish: “Muddling them into the drink does little to improve the flavor or the aesthetics.” Having that knowledge, my current method of muddling both will fall by the wayside as I move forward.

On the subject of "doing it the right way", I can only conclude that there is no definite "one way" to make an Old Fashioned. Personally, I grew up in Wisconsin, moving to Washington at the age of 16. Although I did grow up sitting at the rail of my grandfather's bar, eating the olives out of Grandma's toddies, almost every Friday night of my youth, I knew nothing about cocktails, and most definitely nothing about their preparation. So, imagine my surprise, when upon my return to the Land of Cheese, I ordered an Old Fashioned, and watched the bartender pour a healthy amount of BRANDY in the glass. Being the infant Mixologist that I was at the time, I swiftly corrected her, which in turn had her just as swiftly educating me on a proper Old Fashioned, the Wisconsin-way. Turns out, she had never heard of bourbon being used. She needed to travel a bit, but then again, it was obvious that I did too. One, two, and three Brandy Old Fashioneds later, we were both laughing about our combined lack-of-knowledge, and I was personally wondering how much regional variations there were with cocktails. That will always stick with me, in my profession, and in my travels.

Here are a few variations on the Old Fashioned...


GLASS: Old Fashioned

INGREDIENTS: 3oz bourbon or rye whiskey, Angostura Bitters(3 or 4 dashes), .5oz Simple Syrup(instead of sugar cube, for ease of dissolving), an orange slice, & a cherry(for garnish only now...lol), ice.

TO BUILD: Muddle orange, simple syrup, & bitters in glass, pour preferred whiskey into glass, and a few rocks. Stir, add a few more rocks, stir again, and add a cherry for garnish.

*TIPS: Brandied Cherries make a difference! The use of simple syrup opens an entire world of opportunity, as in different flavors that can be infused into your drink, such as huckleberry, blackberry, lavender, and any other earthly gift that can be made into the sugary ingredient. How to make your own simple syrup


GLASS: Old Fashioned

INGREDIENTS: 2oz brandy, Angostura Bitters(3 or 4 dashes), 1 sugar cube, 1-2 orange slice(s), 2 brandied cherries(for garnish), sweet & sour or seltzer wash, ice.

TO BUILD: Throw orange(s), sugar cube and dashes of Angostura bitters in an empty glass. It must be Angostura. Add a dash of your preferred wash of sweet & sour or seltzer. Just a dash. Don't go overboard here. Flex your forearm, reach for your muddler. Get to pulverizing. Add your preferred brandy to the glass with ice, and stir.

Finish by topping with your preferred wash and garnish with an orange slice and a cherry. 

*TIP: Enjoy while conjuring mental images of the northwoods, the Green Bay Packers, beautiful cheese, charcuterie plates and the Bronze Fonz.


GLASS: Old Fashioned

INGREDIENTS: 3oz tequila(reposado), 2 slices nectarine, 2 Bing cherries, 1 tbsp. agave nectar, Angostura Bitters(2 dashes), Bing Cherry & a nectarine slice(garnishes).

TO BUILD: Place nectarines and agave nectar in the glass, with a couple dashes of the bitters. Muddle well, until the ingredients are thoroughly combined. Add your preferred Tequila Reposado, along with ice, and stir. Garnish and enjoy!

*TIPS: To "lighten" the drink slightly, add a splash of club soda. Grapefruit & dark oranges can be substituted for the nectarine, as they compliment tequila quite nicely!


That's right, and I'm all for it, as everything is better with a little chocolate. The only catch to this tasty treat is that you need to start making it at least 3 days before your first sip. You will begin by infusing one bottle(750ml) Rye Whiskey with 1/4 cup cacao nibs.

How to Infuse Distilled Spirits at Home

GLASS: Old Fashioned

INGREDIENTS: 2.5oz chocolate infused rye whiskey, .5oz demerara syrup (also known as simple syrup. See link above), Bittermens Xocolatl Mole Bitters(3 dashes), half an orange slice, and a brandied cherry.

TO BUILD: Add to the glass the mole bitters, the demerara syrup, the orange slice, and (if you choose) the brandied cherry. Muddle well. Fill the glass with ice and the infused whiskey, stir, (I'll add the cherry as a garnish here), and serve.

*TIP: If you are ever in Boston, swing in to the Franklin Cafe' and personally thank Joy Richard for this recipe. I'd be willing to bet, if she's still there, she'd be happy to make you her Cocoa Old Fashioned!

SPICED RUM OLD FASHIONED... Yo Ho Ho and a bottle of rum!

A sailor be I, and my personal favorite Old Fashioned recipe is most definitely that of the spiced rum kind. Sailor Jerry to be specific.

GLASS: Old Fashioned

INGREDIENTS: 3oz Sailor Jerry Spiced Rum, .5oz demerara syrup, orange bitters(3-5 dashes), and an orange twist(garnish).

TO BUILD: Simply add all ingredients except for garnish to mixing glass filled with ice and stir for 10 seconds. Strain into rocks glass over one large ice cube. Express the orange twist over the glass and drop in. No muddling for this one.

The simple process makes this the ideal boat version!

In closing, I've shared only a few, albeit intriguing, versions of the most American cocktail there is, the Old Fashioned. Let me know in the comments what your favorite mix is. Is it listed above, or something altogether different? If we've learned anything throughout this process, it's that there is no wrong way, and there are many right ones.

"May your anchor be tight, your cork be loose, your rum be spiced and your compass be true." -Danny Taddei

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