Cinnamon Old Fashioned

A warming winter take on the old fashioned, built with bourbon, homemade cinnamon syrup and a perfumed strip of orange peel over a single large ice cube.

Total time
5 minutes
Serves
1
Difficulty
Easy
Base
Bourbon
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Cinnamon old fashioned in a heavy rocks glass with a large clear ice cube, orange peel and cinnamon stick garnish.

Ingredients

serving
  • 60 ml bourbon
  • 10 ml cinnamon-infused simple syrup
  • 2 dashes Angostura bitters
  • 1 large strip of orange peel
  • 1 cinnamon stick (to garnish)
  • 1 large ice cube

Method

  1. Add the bourbon, cinnamon syrup and Angostura bitters to a mixing glass filled with ice.
  2. Stir gently for 25 to 30 seconds until well chilled and properly diluted.
  3. Place a large ice cube into a chilled rocks glass.
  4. Strain the cocktail over the ice cube.
  5. Express the orange peel over the surface of the drink, rub it around the rim and drop it in alongside a cinnamon stick.

How to serve

Glassware
Rocks glass
Serve temperature
Cold
Garnish
Orange peel and cinnamon stick

There is something quietly satisfying about an old fashioned. Three ingredients, one piece of citrus and a moment of patience while you stir. This cinnamon version keeps that minimalism but trades plain sugar for a warm, lightly spiced syrup that turns a familiar drink into something that feels written for December.

The Syrup Does the Heavy Lifting

Cinnamon-infused simple syrup is the only real change from the classic, but it shapes everything. Real cinnamon sticks give a softer, more rounded flavour than ground cinnamon, which can leave the cocktail cloudy and slightly bitter. A ten-minute simmer is enough to draw out the aromatic oils without turning the syrup harsh. Keep it in the fridge and you will find yourself reaching for it in coffee, on porridge and in pretty much every winter drink you make.

When you stir, give it the full thirty seconds. Old fashioneds rely on dilution as much as flavour, and a rushed stir leaves the drink hot and disjointed. Taste a small spoonful before straining; it should feel rounded, faintly sweet and unmistakably warm.

A Spirited Cousin in the Glass

If you enjoy the way warming spices play with a brown spirit, you will probably enjoy what happens when those same spices meet gin and apple. Hot Apple Gin takes a similar idea in a completely different direction, building cinnamon and clove into a hot, fragrant cup rather than a stirred cocktail. The cinnamon old fashioned is the cold, contemplative version; the apple gin is the one you make for friends who have just stepped in from the snow.

Either way, the orange peel is non-negotiable. Express it firmly over the glass so the citrus oils land on the surface, then rub it around the rim before dropping it in.

Frequently asked questions

How do I make cinnamon-infused simple syrup?

Simmer 200 g sugar with 200 ml water and two crushed cinnamon sticks for ten minutes, then let it cool, strain and refrigerate for up to two weeks.

Which bourbon should I use?

A 90 proof bourbon with strong vanilla and caramel notes works best because it stands up to the cinnamon without being overwhelmed by it.

Why a large ice cube?

A single large cube melts slowly, keeping the cocktail cold without watering it down quickly, so the flavour stays balanced for longer.

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