Cream-Filled Chocolate Cherry Cupcakes

That sounds pretty good, doesn't it? It is pretty good. However, I spent quite a bit of time trying to perfect this recipe, getting my ratios and flavors where I thought I wanted them. And even though they are quite good (all 2 dozen were gone in a little over a day), the taste wasn't on par with the level of elevation achieved in my own mind.

Until the second day.

You see, like so many baked goods, the flavors didn't really develop until they had a chance to sit back, relax, and do their flavor-y thing. Where on baking day the cherry flavor was almost indistinguishable, day 2 brought just the right amount of cherry to the shindig. The cake was moister. The cream filling had really set up shop.

Day 2 is where these cupcakes are at.



Cream-Filled Chocolate Cherry Cupcakes
(Makes 2 dozen)

For the cake:
 2 cups sugar
 1-3/4 cups all-purpose flour
 3/4 cup  Cocoa powder
 1-1/2 teaspoons baking powder
1-1/2 teaspoons baking soda
 1 teaspoon salt
 2 eggs
 1 cup milk
 1/2 cup vegetable oil
 2 teaspoons vanilla extract
1 jar maraschino cherries
1/4 c boiling water

Preheat your oven to 350 and line your cupcake tins with cupcake/muffin liners (alternately, you could grease and flour the tins).

First, drain the juice from the jar of cherries, but reserve 3/4 c of it. Finely chop the cherries in a food processor or blender. Set the cherries and juice aside (separately).

Sift all of the dry ingredients together, and mix well. Add all of the wet ingredients (including the mashed cherries), minus the reserved cherry juice, and beat well. Add the boiling and cherry juice, mixing well.

Bake for 25-30 minutes (26 minutes is the exact right time for my oven. Yes, I've made these once or twice). Transfer them to wire cooling racks.


For the filling:
1/2 cup butter
2 cups confectioners' sugar
1/4 tsp salt
3 tablespoons milk
1 teaspoon vanilla extract

While the cupcakes are cooling, make the filling: Cream butter, sugar, and salt together until light and fluffy (this is important). Gradually add the milk and vanilla.


For the frosting:
1 cup Milk
1/2-1 c cocoa powder (depending on how rich you want it. Just keep in mind that it's going on a cupcake that's already pretty decadent. Too much cocoa could be overkill)
5 Tablespoons Flour
1 teaspoon vanilla
1 cup Butter (softened)
1 cup white sugar

Whisk milk and flour over med-medium/high heat in a small saucepan and whisk constantly until the mixture has thickened. Remove from the heat and let it cool to room temperature (I put it in the freezer and stir periodically, so it typically cools in 5 minutes). Once cooled, stir in the vanilla.

Next, cream the butter and sugar until fluffy (3-5 minutes with a hand mixer on medium).  Add the cocoa powder, then the milk/flour mixture and beat until smooth and creamy.

Put it all together: Make sure your cupcakes are cool, otherwise your filling and frosting will just melt.

Now, there's a couple different ways to go about filing the cupcakes. Use whatever method works for you.

Method 1 (The Pastry Bag Poke): Fill a pastry bag with the filling and poke the tip through the bottom or top of the cupcake. Squeeze some filling in. The frosting will hide the hole you created if you poked it through the top.

Method 2 (the Scoop and Shovel): Use a knife (or even a small melon baller) to scoop out a chunk from the center of the muffin (going through the top, not the bottom). Save the cake plug. Use a spoon to shovel in some filling (or use a pastry bag), then replace the plug. The frosting will hide it.

Now that your cupcakes are filled, it's time to frost them. You can do this however you want, but I really prefer piping the frosting on with a pastry bag, because it's easier, quicker, less messy, and looks great. Pastry bags aren't expensive, and have a ton of uses in the kitchen (like making some super simple chocolate eclairs).

Next step: Enjoy, take pictures, and impress your friends with your crazy cupcake prowess.