Spiced Plum Old Fashioned – Bourbon, Plum & Cinnamon Whiskey Cocktail

The Spiced Plum Old Fashioned brings a seasonal shift to a classic whiskey build. Fresh plum adds a soft, jammy fruit note, while cinnamon syrup layers in warmth without overwhelming the bourbon. It stays spirit-forward, but with a rounder, more approachable profile that works well in late summer and early fall.

A Classic with a Seasonal Turn

The Old Fashioned dates back to the early 1800s and is built on a simple formula: spirit, sugar, bitters, and dilution. This version keeps that structure intact while introducing plum and spice as subtle modifiers. Rather than reinventing the drink, it nudges the flavor profile toward cooler weather.

What You’ll Need

Ingredients

• Bourbon – the base spirit, bringing caramel, vanilla, and oak
• Plum – adds natural sweetness and a soft, jammy fruit note
• Cinnamon simple syrup – provides warmth and a controlled sweetness
• Angostura bitters – balances the drink with spice and herbal depth

No fresh plum? Use a small spoon of plum jam or a splash of plum liqueur for a similar effect.

Equipment

• Rocks glass
• Muddler
• Bar spoon

Where This One Stands Out

This version leans into texture and aroma. The plum softens the edges of the bourbon while the cinnamon ties everything together, creating a drink that feels fuller without becoming heavy. It keeps the identity of an Old Fashioned but adds enough variation to feel intentional, not gimmicky.

Substitutions & Variations

• Swap bourbon for rye whiskey for a drier, spicier version
• Use brandy for a softer, fruit-forward profile
• Try orange bitters for a brighter edge or chocolate bitters for depth
• Add a dash of allspice dram for a more pronounced spice profile

Helpful Tips

• Muddle lightly to avoid pulp and bitterness from the plum skin
• Use a large ice cube to control dilution
• Stir long enough to properly chill—this drink benefits from slight dilution
• Express a strip of orange peel over the glass for added aroma