Cinnamon Old-Fashioned Recipe

The old fashioned was invented at the Pendennis Club in 1880s Louisville, where the head bartender built it for bourbon distiller James E. Pepper, who then carried it east to New York’s Waldorf-Astoria and named it after the format he wanted: an old-fashioned whiskey cocktail, not the new ones with vermouth and gum syrup. The cinnamon variant is a 2010s craft-cocktail-revival winter staple. It swaps the standard sugar cube for cinnamon simple syrup, leans on rye instead of bourbon, and finishes with an expressed orange peel that does most of the aromatic work.

What’s on the Bar

An old fashioned is a stirred drink with three components and a peel. The tools are basic but the technique is non-negotiable. A rocks glass with a wide mouth, a long bar spoon (the twisted-handle kind for clean stirring), a Cocktail Kingdom jigger for accurate pours, a large clear ice cube for slow dilution, and good cinnamon sticks for the syrup and garnish.

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Where the Old Fashioned Actually Came From

The Pendennis Club is a private bourbon club in Louisville that opened in 1881, and the prevailing historical record (David Wondrich’s Imbibe!, the gold-standard cocktail history) credits the club’s bartender with the first old-fashioned recipe in writing. James E. Pepper, a Kentucky bourbon distiller and Pendennis member, brought the drink to the bar at the Waldorf-Astoria in New York around 1890, where it picked up the name. The “old-fashioned” qualifier was a customer’s request: he wanted whiskey, bitters, sugar, and water (the original cocktail format), not the more elaborate variations the Waldorf bar was serving in the 1890s.

The cinnamon variant is much newer. It comes out of the post-2008 craft-cocktail revival, when bartenders started experimenting with flavored simple syrups for the winter menu rotation. The cinnamon syrup riff caught on because cinnamon’s warmth meets whiskey’s barrel notes cleanly. It doesn’t fight the spirit the way an orange-spice or chocolate variation can.

Why rye over bourbon for this version: bourbon’s flavor profile leans vanilla, caramel, and oak. Cinnamon adds another warm-baking-spice note, which can stack. Rye whiskey leans pepper, grass, and a touch of mint. The rye’s pepper plays against the cinnamon as a contrast rather than an additive layer. The drink reads sharper, drier, more grown-up.

A Few Notes on the Ingredients

For the whiskey, a 90- to 100-proof rye is the bartender’s pick. Rittenhouse 100 Bottled-in-Bond, Old Overholt Bonded, Sazerac Rye, and Knob Creek Rye all work. If you’d rather use bourbon, choose one with less vanilla and more grain (Wild Turkey 101, Old Grand-Dad Bonded, Buffalo Trace). Skip wheated bourbons (Maker’s Mark, W.L. Weller) here, their soft profile gets buried under the cinnamon.

Cinnamon simple syrup is the heart of the drink. Whole cinnamon sticks broken into the simmer release a deeper, woodier note than ground cinnamon. Ground cinnamon turns the syrup cloudy and grainy. Make a small batch (it keeps for 2 weeks refrigerated) using a 1:1 sugar-to-water ratio with 2 broken cinnamon sticks per cup of water. Steep 10 minutes off heat after the sugar dissolves.

Angostura bitters is the standard, but cinnamon old fashioneds reward a variation. Fee Brothers Aztec Chocolate bitters add a cocoa-cinnamon note that reads like a winter pudding. Bittermens Hellfire Habanero is too aggressive for this drink, but their Spiced Cranberry plays well at holiday parties. Black walnut bitters (Fee Brothers, Berg & Hauck’s) give the cocktail a nuttier base.

The orange peel is doing real work, not garnish work. Use the broadest part of an orange (one wide strip with no white pith). Express the oils by holding the peel firmly between thumb and forefinger and twisting hard over the drink. Then wipe the colored side around the rim of the glass. Skip thin curly peels, they have no oil.

The ice cube matters. A large clear cube (one big cube per drink) melts slowly and gives the drink its smooth stirred texture. Standard fridge ice melts too fast and over-dilutes. A cube-mold tray or a sphere mold both work.

Recipe: Cinnamon Old Fashioned

Prep time: 4 minutes per drink | Cinnamon syrup time: 15 minutes (one batch, makes 16 drinks’ worth) | Total time: 19 minutes | Serves: 1 (scale up by multiplying)

Ingredients

For the cinnamon simple syrup (makes about 240 ml / 1 cup)

• 200 g (1 cup) granulated sugar
• 240 ml (1 cup) water
• 2 cinnamon sticks, broken in half

For one cinnamon old fashioned

• 60 ml (2 ounces) rye whiskey (Rittenhouse 100 or Old Overholt Bonded)
• 7.5 ml (1/4 ounce, 1 1/2 teaspoons) cinnamon simple syrup
• 2 dashes Angostura bitters
• 1 dash Fee Brothers Aztec Chocolate bitters (optional)
• 1 large clear ice cube (about 5 cm / 2 inches)
• 1 wide orange peel (no white pith)
• 1 cinnamon stick, for garnish (optional)

Instructions

1. Make the cinnamon simple syrup. Combine 200 g (1 cup) sugar, 240 ml (1 cup) water, and the 2 broken cinnamon sticks in a small saucepan over medium heat. Stir until the sugar dissolves, about 3 minutes. Take it off the heat, cover, and let it steep for 10 minutes. Strain into a sealed jar. Cool fully before using.
2. Place the 1 large ice cube in a rocks glass. Pour in the 60 ml (2 ounces) rye whiskey, 7.5 ml (1/4 ounce) cinnamon simple syrup, 2 dashes Angostura bitters, and the dash of Aztec Chocolate bitters if using.
3. Stir with a long bar spoon. Hold the spoon vertically against the glass and rotate, keeping the spoon in contact with the ice. Stir for about 20 to 30 seconds, until the outside of the glass feels cold and the drink has lightly diluted. You want the smooth-textured mouthfeel of a stirred drink, which is what separates a real old fashioned from a shaken one.
4. Hold the wide orange peel firmly between your thumb and forefinger, colored side down, about 3 cm (1 inch) above the surface of the drink. Twist hard. The peel will release a fine spray of citrus oil onto the cocktail’s surface. You should see a brief mist.
5. Wipe the colored side of the peel around the rim of the glass. Drop the peel into the drink, or perch it on the rim. If using, lay the cinnamon stick across the top of the glass as a second aromatic garnish.
6. Serve immediately. The drink should taste whiskey-forward with a clear warm-spice note in the middle and a citrus-oil lift at the rim.

Notes

Stir, do not shake. Shaking an old fashioned introduces air, over-dilutes the spirit, and gives the drink a milky-foam top. The cocktail loses its texture. This is the iron rule that separates old fashioneds in working cocktail bars from old fashioneds at chain restaurants.

If you don’t have a large ice cube mold, use the biggest cube your tray makes and accept slightly faster dilution. Crushed ice is the wrong direction here, the drink dilutes in 90 seconds and reads thin.

The cinnamon syrup keeps for 2 weeks refrigerated in a sealed jar. After 2 weeks the cinnamon’s aromatic oils break down and the syrup tastes flat. Make small batches.

Tips and Variations

Bourbon swap: pick a grain-forward bottle

If you only have bourbon, pick one with less vanilla sweetness. Wild Turkey 101, Old Grand-Dad Bonded, and Buffalo Trace all keep enough grain character to stand against the cinnamon. Avoid wheated bourbons (Maker’s Mark, Weller, Larceny) in this drink, their soft profile disappears under the spice.

Muddled cinnamon stick variant

For a coarser, woodier version, skip the simple syrup. In the bottom of the rocks glass, muddle a 1-inch broken piece of cinnamon stick with 1 sugar cube and 2 dashes of Angostura until the sugar partly dissolves and the cinnamon releases its oil. Add ice and rye and stir. The drink reads more bitters-bar than craft cocktail, with the cinnamon’s woodiness more present.

Smoked cinnamon stick presentation

For the photo: torch the end of a cinnamon stick with a kitchen blowtorch until it smokes (about 5 seconds). Lay the smoking stick across the glass for 30 seconds with a small cocktail-smoking dome on top, then remove. The drink picks up a subtle campfire note. Worth it for one or two presentation drinks. Not worth it for a batch.

Apple-cinnamon riff for fall

Add 15 ml (1/2 ounce) of fresh unfiltered apple cider to the drink along with the syrup. Reduce the rye to 45 ml (1 1/2 ounces). The result is a softer, slightly sweeter cocktail that reads more like a fall warm-up than a winter sipper. Good for an early-November party.

Make-ahead and storage

Cinnamon syrup: 2 weeks refrigerated. The drink itself doesn’t batch well, the stirred dilution is part of the build. For a party, pre-measure rye and syrup into a jug at room temperature (no bitters, no ice, no peel). Pour 67.5 ml (2 1/4 ounces) into each glass over a large ice cube, finish with bitters and the peel one at a time.

Glassware, Garnish, and When to Pour

A wide rocks glass (200 to 300 ml capacity) is the format. The wide mouth lets the orange-peel oil reach the drinker before each sip. The thick base sits well in the hand. Skip tall glasses, Collins glasses, and stemmed glasses for this drink, the format is the format.

The orange peel is the only mandatory garnish. The cinnamon stick is optional and adds visual lift. A Luxardo maraschino cherry is a controversial third option (some bars use it, some don’t). If you add the cherry, drop it into the glass before the ice so it sits at the bottom.

When to serve: cold-weather dinners, Christmas Eve, New Year’s Eve, holiday parties, after-dinner sipping by a fireplace. The drink rewards a slow drinker. Pair with sharp aged cheddar, dark chocolate, dried figs, smoked almonds, or a small plate of cinnamon-sugar pastries.

Frequently Asked Questions

What’s the best whiskey for a cinnamon old fashioned?

A 90- to 100-proof rye is the bartender’s preference. Rittenhouse 100, Old Overholt Bonded, Sazerac Rye, and Knob Creek Rye all work. The rye’s pepper plays against the cinnamon better than bourbon’s vanilla. If you’re using bourbon, pick a grain-forward bottle (Wild Turkey 101, Buffalo Trace), not a wheated one.

How do you make cinnamon simple syrup?

Combine equal parts sugar and water (1 cup each) in a saucepan with 2 broken cinnamon sticks. Stir over medium heat until the sugar dissolves, about 3 minutes. Take it off the heat, cover, and steep for 10 minutes. Strain into a sealed jar. Keeps 2 weeks refrigerated.

Is an old fashioned stirred or shaken?

Stirred, always. Shaking introduces air and over-dilution, both of which kill a spirit-forward cocktail. Stirring with a bar spoon for 20 to 30 seconds gives the drink the smooth stirred texture that the format requires.

Can I use ground cinnamon instead of cinnamon sticks?

Not in the syrup. Ground cinnamon turns the syrup cloudy and grainy, and the texture won’t strain out. Whole cinnamon sticks broken into the simmer pull the aromatic oils without the grit. They’re the only way to get a clean cinnamon syrup.

How long does cinnamon simple syrup last?

Two weeks refrigerated in a sealed glass jar. After 2 weeks the cinnamon’s aromatic oils break down and the syrup loses its lift. Make small batches and use them within the window.

Final Thoughts

The cinnamon old fashioned is a winter cocktail done right when the format respects the format. Whiskey, syrup, bitters, peel, and ice. Anyone who shakes it is making a different drink.

If the cinnamon syrup is already in the fridge, the drink takes 4 minutes to build. Make the syrup once at the start of the season and pour cinnamon old fashioneds through December and January without rethinking anything. The Pendennis Club bartender in 1881 would recognize the drink. That’s the point.

Last update on 2026-08-08 / Affiliate links / Images from Amazon Product Advertising API