Chocolate Cupcakes with Raspberry Filling

by Michelle

Chocolate cupcakes with raspberry filling are a delicious and decadent treat! The combination of rich chocolate cake and tart raspberry filling is a match made in heaven. Plus, they’re easy to make and perfect for any occasion.

Funny how family traditions are rarely questioned. Celebrating Valentine’s Day is a given in my world. Has been all my life. I remember making homemade Valentines to give to my little brother and to my parents before I’d started school.

Why would a child under the age of six, before the Internet and the influence of television – we had one channel in black and white – know to make a Valentine’s Day card.

It was Dad.

I’ve watched my dad give my mom profoundly intimate cards of love for as long as I can remember. Before I could read, I had to be satisfied with her delighted response, “that’s between me and your father” when I asked what the card said. Once old enough to read, I’d secretly peek at the message, when I was alone. Although the words were intended for my mom, the feelings they invoked in me were profound.

Paper Doile

Dad is a quiet man. More so when he was young. As a child, my parents were physically affectionate with one another – they still are for that matter… – but their language was full of the business of the day. Discussions about our families daily activities, how the car was working, what we needed for groceries, regular family stuff. But every February 14th, Dad would speak from a secret place in his heart, for the love he felt for my mom, through a Hallmark card decorated with hearts and cupids. Those lovely, sometimes corny, messages made me feel like the luckiest little girl in the world. I knew that my parents loved each other but having it captured, in a store bought card, where I could read and reread left me empowered by the knowledge.

Knowing that your parents share a deep and meaningful love creates a confidence that lasts a lifetime.

Without question, the tradition carried on in my home. Valentine’s day cards, pretty heart shaped cakes and cupcakes were the order of the day. I have so many memories of the girls, waiting with bated breath, while I opened my Valentine’s Day gift from Ralph. Their faces flushed with excitement, they’d ask me to read my card aloud. When I finished, they’d run into Ralph’s arms and shower him with kisses. We always had little cards and treats for them but Ralph’s gift to me seemed always to be more thrilling. Until today, I’d never given those lovely Valentine moments much thought. I realize, now, my daughters were experiencing the same joy that I did as a child. To bare witness to your parent’s love is powerful. Seeing it amidst heart shaped cakes, flowers and whimsical poems, to a child, is magical.

I know the sentiment exists that Valentine’s day is a retail celebration and does nothing more than make simpering references to a vague concept called ‘love’ but I, most respectfully, disagree.

Chocolate Frosting

Chocolate Cupcakes with Raspberry Filling
makes 18 cupcakes
preheat oven 350*F

1/2 cup butter
2 cups granulated sugar
2 extra-large eggs
1 teaspoon pure vanilla extract
2 2/3 cups all-purpose flour
1/2 cup best quality cocoa I use Bendorp Dutch processed cocoa
2 teaspoons baking soda
1 teaspoon salt
2 cups sour whole milk if you don’t have soured milk on hand, place 2 tablespoons of white vinegar in the bottom of a 2-cup measure then add the milk up to the 2-cup line
Homemade raspberry jam for filling
Chocolate Frosting – recipe to follow


  • Line muffin tin with paper liners
  • Sift flour, cocoa, baking soda and salt together and set aside.
  • Beat sugar with shortening until it is light and fluffy.
  • Beat in eggs one at a time
  • Add vanilla and beat well.
  • Fold the milk with the flour mixture alternatively in thirds into the butter mixture…blend well
  • Fill paper liners 2/3 full – resist the urge to over fill the paper liners!
  • Check at 25 minutes by inserting a wooden toothpick in the centre of a cupcake. They are done when the toothpick comes out clean.
  • When done, remove from oven and take out of muffin tin.
  • Allow cupcakes to cool on a wire rack.
  • Frost when completely cool.

These cupcakes should be stored in the refrigerator or can be frozen, well wrapped, up to 4 months. I even freeze them frosted!

THE LOVE: Have all of your ingredients at room temperature. My mother swears by it!

click for printable recipe


Chocolate Frosting
Makes enough to frost an 8” layer cake or 18 cupcakes

2 ½ cups icing sugar
½ cup cocoa I used Dutch processed Bensdorp cocoa
1/3 cup butter, softened
¼ cup milk
1 teaspoon vanilla


Place all ingredients in the bowl of your stand mixer and beat until fluffy and light

THE LOVE: Scrap the bowl several times during the beating process to make sure you don’t end up with any streaks.

click here for printable recipe

Heart Tray

one year ago: baby bok choy with ginger and chilies

two years ago: rich root vegetable and boursin soup

Thanks for reading.