Preheat your oven to 350°F (175°C) and line a 12-cup muffin tin with cupcake liners.

In a large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy. Add the eggs one at a time, mixing well after each addition. Stir in the vanilla extract.

In a separate bowl, whisk together the flour, baking powder, and salt. Gradually add the dry ingredients to the wet mixture, alternating with the milk, starting and ending with the flour mixture. Mix until just combined.

Divide the batter evenly among the prepared cupcake liners, filling each about two-thirds full. Bake for 18-20 minutes or until a toothpick inserted into the center comes out clean. Allow the cupcakes to cool in the pan for 5 minutes before transferring them to a wire rack to cool completely.

While the cupcakes are cooling, prepare the cream filling. In a medium bowl, whip the heavy cream, powdered sugar, and vanilla extract until soft peaks form. Once the cupcakes are cool, use a small knife or a cupcake corer to remove a small portion from the center of each cupcake and fill with the whipped cream mixture.

For the chocolate ganache, heat the heavy cream in a small saucepan over medium heat until it just begins to simmer. Remove from heat and pour over the chocolate chips in a bowl. Let it sit for a minute, then stir until smooth.

Drizzle the chocolate ganache over the filled cupcakes. Allow the ganache to set for about 15 minutes before serving.