HELLO LOVER.

I’ve taken the classic bourbon smash and bumped it up with pumpkin pie flavors. Imagine that same bright, boozy cocktail but with warm pumpkin, cozy spice and a whisper of vanilla — basically a slice of pumpkin pie in a glass. If you want full dessert-level indulgence, pair it with a piece of pie topped with bourbon-whipped cream. Pumpkin pie cocktail inception.

Yes, I know I’ve been obsessed with pumpkin this season — maybe to the point of overkill — but this cocktail is worth it. It’s the perfect fall sipper: indulgent and dessert-like, but not cloyingly sweet or heavy enough to ruin your dinner.

The base is a homemade pumpkin pie syrup — yes, pie syrup. It’s simple to make and far more balanced than many commercial pumpkin-spice products because you control the seasoning. I first used this syrup in my pumpkin coconut hot chocolate and loved how flavorful it was without being overly spiced. I actually made the syrup for this cocktail originally and had leftovers that were perfect for other drinks and desserts.

This cocktail feels special for holidays like Friendsgiving. It’s easy to make in small batches — you can build a pitcher for four to six people if you prefer — but it’s not the best candidate for very large make-ahead batches. If you want something you can prep days ahead and serve to a crowd, consider a cider- or apple-based sangria or a sparkling punch instead, which hold up better over time.
What are you serving for Friendsgiving this year? Any cocktails on the menu?

Part of why I love this cocktail is that it’s the kind of thing you usually make for a gathering rather than a regular weekend night. Rally a few friends, make the syrup ahead if you want, and assemble over crushed ice when guests arrive. It’s served on the rocks — not frozen or creamy — which keeps it bright and refreshing while still feeling autumnal.

Honestly, if it were up to me, we’d all enjoy our pie as a cocktail.

Pumpkin Pie Smash Cocktail
Yield:
1
makes 1 drink, is easily multiplied
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Ingredients
Pumpkin Pie Syrup
- 1 cup sugar
- 1 cup water
- 1/3 cup pumpkin puree
- 1/4 to 1/2 teaspoon pumpkin pie spice
- 1/2 teaspoon vanilla extract
Pumpkin Pie Smash
- Crushed ice
- 2 to 3 tablespoons pumpkin pie syrup
- 2 dashes cocktail bitters
- 2 ounces bourbon
- Cinnamon stick for garnish
Instructions
Pumpkin Pie Syrup
- Heat the sugar, water, pumpkin puree and pumpkin pie spice in a saucepan over medium-low heat. Whisk constantly until the sugar dissolves and the mixture comes to a gentle simmer. Remove from heat and let cool slightly, then stir in the vanilla extract. Strain through a fine-mesh sieve to achieve a smooth, syrupy consistency. Store in a sealed container in the refrigerator for up to a week.
Pumpkin Pie Smash
- Fill a chilled glass with crushed ice. Add 2 to 3 tablespoons pumpkin pie syrup and 2 dashes bitters. Pour in 2 ounces bourbon and stir gently to combine. Garnish with a cinnamon stick and serve.
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I appreciate you so much!

Or at least with pie on the side. Always.