Dark Chocolate Cherry Cupcakes


I made these delicious cupcakes for Valentine’s Day this year. That was weeks ago, I know! But, better late than never, right? The past few weeks have been crazy! Between a busy work schedule, going on vacation, and GETTING ENGAGED my time has been very consumed (in the best way possible)! While John and I have been sitting down to the computer together to look at wedding venues (eeek!), this is the first time in  weeks that I have sat down at the computer to write. Sad, but true. In the coming weeks I am looking forward to sharing all of our wonderful St. Croix vacation photos (plus some of the surprise engagement shoot photos) with you! Stay tuned!

Back to the cupcakes- I have to say, I think this is the best gluten free dessert that has come out of my kitchen! The cupcakes were flavorful, moist, and had the perfect (non-gluten free) consistency which can be really tough with GF baking. While they were not hard to make, they were not easy either. Cutting out the center of the cupcakes and trying to get the tops back on after I filled them was tedious. I suppose you could probably not worry about putting the top back on if you knew they were all going to be eaten that same day. Otherwise I worry the filling would leak out and make the frosting funky. Thanks, but no thanks.


For the Cupcakes
  • 3 oz bittersweet chocolate, finely chopped
  • 1/3 cup (unsweetened) cocoa powder
  • 3/4 cup hot water
  • 3/4 cup gluten free flour
  • 3/4 cup sugar
  • 1/2 tsp salt
  • 1/2 tsp baking soda
  • 1/4 cup + 2 Tbsp vegetable oil
  • 2 eggs
  • 2 tsp white vinegar
  • 1 1/2 tsp vanilla extract
For Filling
  • 1 large jar cherry pie filling (I used a local Door County pie filling)
For Frosting
  • 1 cup butter, softened
  • 3-4 cups powdered sugar
  • 1/2 cup cocoa powder
  • 1-2 Tbsp milk
  • 1 tsp vanilla


  1. Preheat oven to 350 degrees. Place the chocolate and cocoa powder in a medium bowl, then pour hot water over chocolate mixture and whisk until smooth. Place the bowl in the refrigerator to chill (20 minutes or 10 in freezer).
  2. While the chocolate is chilling, in a medium mixing bowl, whisk together flour,  sugar, salt and baking soda. In a separate mixing bowl, whisk together oil, eggs, vinegar and vanilla.
  3. Once the chocolate has cooled pour it into oil mixture and stir until well combined, then add flour mixture and whisk until silky smooth.
  4. Pour the batter into paper lined cupcake tin (12 count). Bake in preheated for 17 – 19 minutes. You can check  if they are done by inserting a toothpick into the center of a cupcake, if it comes out clean they are done!
  5. Allow cupcakes to cool in baking tin for a few minutes before you transfer to a wire rack. Allow the cupcakes to cool completely before you try to cut them out. If you don’t wait, the cupcakes will be very difficult to cut not to mention impossible to frost!
  6. With a small sharp knife cut a hole in the center of each cupcake. You want to make them big enough and deep enough to be able to add about 2 tablespoons of pie filling to each. Note: you can trim the bottom part (actually the top of the cupcake) that you cut out so it sit flat when you put the tops back on!
  7. For the frosting, in a large mixing bowl add butter and beat until it’s whipped. Add in the first 3 cups of sugar, cocoa powder, 1 tablespoon milk, and vanilla extract. Beat this on low-medium until creamy. Note: If the frosting is runny add more  powdered sugar, if the frosting thicker than you would like add more milk.
  8. Using an icing bag (or cut the tip off of a Ziploc baggie) and frost your cupcakes. Top with cherry and enjoy!


Bon appétit!


4 thoughts on “Dark Chocolate Cherry Cupcakes

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