“Boo”zy Chocolate Covered Raspberry Cupcakes


A little Halloween trivia for y’all.

Q: What’s red, black, and boozy all over?

No, this is not a trick. The answer, however, IS a treat…


A: These cupcakes!

Congratulations, you cracked the code. But with chocolate, raspberry filling, and some crafty booze infusion, these could really be the answer to practically any question you ask. What, were you expecting an actual joke? I told you it wasn’t a trick. Let’s leave the Halloween punchlines to Buzzfeed (seriously #7 – how can you not at least chuckle?) and I’ll just do what I do best – fatten you up for fall. Sound good? Thought so. Let’s proceed.


These are to-DIE-for. Dark and mysterious with unexpected twists and turns, they’re everything a Halloween cupcake should be. The cupcakes are a deep, dark-as-night chocolate topped with a spoonful of rich chocolate ganache. Watch out though, the tart-but-sweet raspberry filling buried inside may jump out at you without warning. And that added presence you sense lingering around? Spirits. Red wine and Chambord, to be exact. I don’t care who you are, these treats will keep you on your toes and constantly wondering whether the next bite might get you (don’t worry – that oozing red stuff is just the raspberry filling).

While the flavors are very Halloween-esque, these wouldn’t be complete if they didn’t look the part too. This holiday is all about costumes, so I couldn’t deprive these little guys of dressing up accordingly. I picked a few options and mixed it up because, well, Halloween should be anything but predictable. Plus I wanted to try out some new icing colors and decorating techniques I’d seen around the ‘gram. On one of my Target breaks, I snagged some adorable Wilton cupcake toppers, along with some neon gel food coloring that I knew would give me the bright purple and orange hues I was envisioning. I opted to do a traditional swirl with the toppers, but also threw in some two-toned icing and spider web designs for some variety.

DSC_0162These were so fun to decorate, and even more fun to eat. While they have a depth of flavor (dare I say six feet deep?), they’re not too heavy at all. The red wine chocolate cake is actually a little lighter and fluffier than I prefer when I’m adding a filling, but it worked out just fine. If you’re not a fan of dense cake, then you’ll actually love this recipe. The chocolate ganache was a fun added touch, but didn’t pile on the richness. And then this raspberry Chambord buttercream – perfect. Chambord is probably my favorite liqueur (hence my love of French martinis), so I was perfectly fine stocking up just for the sake of the frosting. Verdict is that everything worked together wonderfully. A few people even said that they normally don’t like fruit in cupcakes, but that the raspberry filling in these was great. I suspect it’s because the tartness of the raspberries plays well with the sweetness of the chocolate. Either way, mission accomplished.

With Halloween upon us, the inevitable “I die” reaction these Red Wine Cupcakes with Raspberry Chambord Buttercream will evoke has never been more appropriate. The most frightening part? When the last one is eaten. The thought alone is a nightmare – the kind that may haunt you foreve- well, until you make the next batch. As Dracula might say, it’ll be love at first bite. I promise.


Chocolate Covered Raspberry Cupcakes

Red Wine Cupcakes (from Wine Dine & Wander):

1 1/2 cups all-purpose flour
1 1/2 cups white sugar
1/2 cup dark cocoa powder
1 1/2 teaspoons baking soda
1 1/2 teaspoons baking powder
2 teaspoons cornstarch
1 teaspoon salt
2/3 cup buttermilk
1/2 cup + 2 tablespoons red wine (I used a Zinfandel)
1/3 cup + 1 tablespoon vegetable oil
2 eggs, room temperature, lightly beaten
1 tablespoon pure vanilla extract

Raspberry Filling (from Living Better Together):

4 cups frozen raspberries
1 cup sugar
4 tbsp cornstarch
3 tbsp water

Chocolate Glaze (adapted slightly from Kelly Bakes):

4 oz semi- or bittersweet chocolate (I used 60%)
4 tablespoons heavy cream
2 teaspoon corn syrup

Raspberry Chambord Buttercream (from I Heart Cuppycakes):

1/2 cup solid vegetable shortening
1/2 cup (1 stick) butter, room temperature
1/2 teaspoon raspberry extract
1 lb (4 cups) powdered sugar, sifted
1-2 tablespoons milk, as needed
1-3 teaspoons Chambord, to taste (I used 3! Obviously.)


1. Before you’re actually ready to bake your cupcakes, prepare your filling (this can even be done a day or two ahead of time). Put frozen raspberries in a medium pot and heat on medium-high until berries boil down, probably about 10-15 minutes. Once raspberries come to a boil, stir in sugar, and return to a boil. Add corn starch and water to a separate bowl and stir together. It will be really thick, but just mix until incorporated and pour into the raspberries. Stir vigorously for 1 minute, or until sauce thickens. Remove from heat and allow to cool completely. It will continue to thicken as it cools. I chilled mine for a few hours in the fridge before using to thicken it up some more, but you can use it right away if you’d like.

2. Time for the cupcakes. Preheat oven to 350 degrees and line 2 cupcake pans with liners of your choosing. In the bowl of electric mixer fitted with the paddle attachment, add flour, sugar, cocoa powder, baking soda, baking powder cornstarch and salt, and whisk to incorporate. In a medium bowl, combine the buttermilk, wine, oil, eggs and vanilla. Add the liquid mixture to the dry ingredients and mix for about 2 minutes on medium speed. Fill cupcake liners about 2/3 of the way full. Note that the batter will be thin, but that’s ok! The cupcakes will be fine, I promise. Bake for 15-17 minutes, or until the toothpick inserted into the center comes out clean. Allow to cool for a few minutes and then remove to wire racks to cool completely.

3. When the cupcakes are cooled down a bit, fill them with the raspberry filling. Use a paring knife to core a little cone out of the center of each cupcake, trimming the end off of the piece you removed so that you have a small disc topper remaining. Fill the cupcake with a spoonful of raspberry filling, and replace the little disc topper to close the hole.

4. Onto the glaze. Chop the chocolate and add to a medium bowl. Add the heavy cream to a separate microwave-safe bowl and heat for 30 seconds, or until the cream just begins to bubble. Pour the cream over the chocolate and whisk vigorously to melt. Once it’s combined, whisk in the corn syrup. Once fully incorporated, spread a small spoonful onto each cupcake, covering the surface and creating a sort of shell to cover the part you filled. Allow to cool completely (you can also stick them in the fridge to accelerate that process) before frosting.

5. Now for this frosting. In a stand mixer fitted with the paddle attachment, cream shortening and butter until smooth (I mixed for about 2 minutes). Gradually add powdered sugar about 1/2 cup at a time, beating to combine after each addition. Add milk 1 tablespoon at a time as needed, until buttercream is light and fluffy. Add raspberry extract and Chambord and beat until smooth.

6. Fill a piping back with frosting and pipe onto cupcakes as desired.

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