Why does autumn always scream plums to me? Maybe because I used to have a yellow plum tree when we lived in Seattle and it would ripen in late summer/ early fall. Or maybe because this stone fruit roasts up so beautifully and pairs with warm spices so well.
The Roasted Plum Cinnamon Smash is rich, sultry, and just the right amount of cozy — like sipping autumn by the fire. Roasted plums bring a jammy sweetness, while cinnamon syrup adds warmth and spice. Bourbon rounds it out with that classic caramel depth we all crave when the weather turns crisp.
It’s a drink that feels both rustic and refined, perfect for evenings when you want something seasonal but unexpected. I made this one for friends while we handed out candy this past Halloween, and it was a massive hit as the temperatures dropped into the high 60s here in SoCal.
And yes, the 60s are chilly for us. If we get into the 50s, my heat is on, and so is a coat. Our blood thins out a bit out here. Ha!
What Makes This Cocktail Special
This cocktail layers flavors beautifully: roasted stone fruit, gentle spice, and oak-aged bourbon all working in harmony. The roasting process intensifies the plums’ natural sweetness while adding a hint of caramelization that pairs perfectly with bourbon. The lemon juice keeps things bright and from getting too “syrupy,” while cinnamon syrup ties it all together with a bit of warmth.
Roasted Plum Cinnamon Smash Recipe
Ingredients
- 2 oz bourbon
- 1 oz roasted plum syrup
- 0.5 oz lemon juice
- 0.25 oz cinnamon syrup
- 2 dashes aromatic bitters (optional but highly recommended)
Instructions
- Combine all ingredients in a cocktail shaker filled with ice.
- Shake vigorously until well chilled.
- Strain into a rocks glass filled with crushed ice.
- Garnish with a roasted plum slice, lemon twist, and/or cinnamon stick.
Give It A Twist!
Add a bar spoon (about 1/8 oz) of aged balsamic vinegar for a rich, tangy depth that amplifies the roasted fruit flavors.
For an extra layer of complexity, add a half-ounce splash of orange liqueur like Cointreau or Grand Marnier before shaking. This subtle citrus addition bridges the gap between the bright lemon and the deeper fig notes, creating an even more nuanced cocktail.
Mocktail Version
Replace the bourbon with a strong black tea concentrate (such as Assam or English Breakfast). It keeps the dark, tannic backbone while allowing the roasted plum and cinnamon to shine.
Homemade Roasted Plum Syrup
Roasted plum syrup is easy to make and worth every step. Halve ripe plums, sprinkle with a little brown sugar, and roast at 400°F for about 20–25 minutes until soft and caramelized.
Combine with water and sugar in a saucepan, simmer for 5–10 minutes, then strain. Chill before using.
The Mocktail Version
Not drinking alcohol? Replace the bourbon with 2 ounces of strong black tea concentrate—something robust like English Breakfast or Assam works, but not Earl Grey which has it’s own botanical flavors.
The tea’s tannins mimic the structure of bourbon, while its malty notes complement the roasted plum wonderfully. Follow the same recipe, and you’ll have a sophisticated alcohol-free sipper that doesn’t compromise on complexity.
Bourbon Selection
Choose a bourbon with enough character to stand up to these bold flavors. A higher-proof bourbon (90-100 proof) won’t get lost, and one with noticeable vanilla and caramel notes will harmonize beautifully with the roasted fruit. Brands like Buffalo Trace, Woodford Reserve, or Wild Turkey 101 all work wonderfully here. Avoid anything too delicate—you want a bourbon with personality.
Tips for Success
Use fresh lemon juice. The brightness is essential to balance the rich, sweet roasted plum. Bottled lemon juice will make this cocktail taste flat and one-dimensional.
Don’t skip the crushed ice. It transforms the texture and drinking experience. If you don’t have a Lewis bag and mallet, pulse ice cubes in a blender or wrap them in a clean kitchen towel and smash with a rolling pin.
Quality cinnamon syrup matters. Look for cinnamon syrup made with real Ceylon cinnamon, or make your own by simmering cinnamon sticks in simple syrup for 20 minutes. The cheap stuff tastes artificial and will throw off the whole drink.
Temperature is everything. This cocktail should be served ice-cold. Don’t rush the shaking—a full 15-20 seconds ensures proper dilution and temperature.
