If you’re looking for a fall and winter Old Fashioned that leans fruity without turning into a dessert cocktail, the Plum Bourbon Old Fashioned is a perfect fit. It was one of the favorites at our Halloween party this year too.
Roasted plums bring out deep jammy notes—think dark fruit, caramelized edges, and a hint of tartness—while bourbon (or rye) adds backbone and warmth. A couple of dashes of bitters tie everything together so the drink stays balanced, classic, and spirit-forward. I couldn’t make this one fast enough for friends.
Plum Bourbon Old Fashioned Recipe
Glass: Rocks glass (with a large ice cube)
Ingredients
- 2 oz bourbon or rye
- 0.5 oz roasted plum simple syrup
- 2 dashes aromatic bitters or cardamom bitters
- Orange peel
Instructions
- Add bourbon (or rye), roasted plum syrup, and bitters to a mixing glass filled with ice.
- Stir until well chilled and properly diluted—about 20–25 seconds.
- Strain into a rocks glass over one large ice cube.
- Express an orange peel over the drink to release the oils, then drop it in.
- Optional: lightly torch the orange peel before expressing for a smoky, caramelized aroma.
How to Make Roasted Plum Simple Syrup
This syrup is the heart of the cocktail—rich, slightly tart, and full of roasted flavor.
Ingredients
- 3–4 ripe plums, halved
- 1 cup sugar
- 1 cup water
Method
- Roast plums at 400°F for 20–25 minutes until soft and caramelized.
- Combine roasted plums, sugar, and water in a saucepan.
- Simmer 10 minutes, mash lightly, and let cool.
- Strain through a fine mesh strainer.
Keeps 1–2 weeks in the fridge, or freeze it in small batches to use when needed.
Flavor Notes
- Bourbon gives you warm vanilla and caramel.
- Rye creates a spicier, more energetic version.
- Plum syrup brings depth—jammy, rich, and slightly tangy.
- Cardamom bitters add a subtle floral spice that pairs beautifully with roasted fruit.
This isn’t a sugary fruit cocktail—it’s still very much an Old Fashioned, just with a softer, more complex sweetness.
The Twist
Want even more depth?
- Lightly torch the orange peel before expressing.
- OR smoke your glass first for a campfire, winter-lodge vibe.
Mocktail Version
A non-alcoholic Old Fashioned that actually feels grown-up:
- Replace bourbon with non-alcoholic whiskey or strong chilled black tea.
- Use roasted plum syrup and bitters as usual (or NA bitters if preferred).
- Stir with ice and strain over a large cube.
- Garnish with an orange peel.
The tannins from black tea mimic the dryness of whiskey… to a degree.
Home Bar Tips
Use a large, clear ice cube.
Slower melting → better sipping. It keeps the Old Fashioned from becoming watery. I use this ice cube tray to get clear ice every time.
Don’t oversweeten.
The roasted plum syrup is rich. Start with 0.5 oz and adjust next time if you want more fruit.
Choose your bitters wisely.
- Aromatic bitters = classic Old Fashioned feel
- Cardamom bitters = warmer, more holiday-friendly
- Orange bitters = brighter and citrus-forward
Express properly.
Squeeze the orange peel over the drink to release the oils—it makes a huge difference.
What If I Don’t Have…?
No roasted plum syrup?
Try these:
- Black cherry syrup
- Blackberry syrup
- Fig syrup (warm and earthy)
- Regular simple syrup + muddled plum (not the same, but works)
No bourbon?
Rye is fantastic.
Brandy makes a beautiful winter version.
Dark rum will give a richer, sweeter twist.
No orange peel?
Use a lemon peel for brightness.
Or skip it—plum + bitters + bourbon already have great complexity.
Troubleshooting
“It’s too sweet.”
- Use 0.25 oz syrup instead of 0.5 oz
- Add an extra dash of bitters
- Use rye instead of bourbon for more bite
“It’s too strong.”
- Stir longer for more dilution
- Add a small splash of water (⅛ oz) to soften alcohol edges
“The plum flavor is too light.”
- Increase syrup slightly
- Use cardamom bitters
- Make sure your plums were fully ripe before roasting
“My syrup turned cloudy.”
Totally normal—fruit syrups often do. Double strain if you want a clearer look.
