Step-by-Step Method:

Muddle the Cherries and Syrup:

In a mixing glass, add 2 black cherries and 1 tsp of black cherry syrup. Use a muddler to gently mash them together, releasing the rich flavors from the cherries. From my own personal experience, muddling too hard can make the drink bitter, so be gentle.

Add the Bourbon and Bitters:

Pour 2 oz of bourbon into the mixing glass along with 2 dashes of Angostura bitters. The bitters add depth to the drink, balancing the sweetness of the black cherry syrup.

Stir with Ice:

Add a few ice cubes (or one large ice cube) to the mixing glass. Stir the mixture for about 20-30 seconds to chill the drink thoroughly and dilute it just enough for a smooth sip. Based on my overall experience, this is where you control the strength of your Old Fashioned, so adjust the stirring time to your preference.

Strain and Serve:

Using a strainer, pour the mixture into an Old Fashioned glass with a large ice cube or several smaller ice cubes.

Garnish:

Express the oils from a fresh orange peel over the top of the drink and drop it into the glass. This adds a zesty aroma to complement the drink's cherry sweetness.

Variations & Substitutions:

Dietary needs: For a lower-sugar option, you can substitute the black cherry syrup with a sugar-free cherry-flavored syrup or muddle fresh cherries without syrup. This reduces the overall sugar content while still giving you that black cherry flavor.

Whiskey alternatives: If you’re not a bourbon fan, try rye whiskey for a spicier version or even rum for a Caribbean twist.

Bitters: Swap out the Angostura bitters for cherry bitters to intensify the black cherry flavor, or try orange bitters for a more citrus-forward experience.

Smoky finish: Add a dash of smoky scotch or mezcal to give the drink a slight smokiness, adding a layer of complexity.