Preheat the oven to 350°F and line a cupcake pan with four paper liners.
In a medium bowl, whisk together the flour, black cocoa powder, granulated sugar, baking soda, and salt.
In a separate bowl, mix the buttermilk, vegetable oil, egg, and vanilla extract until smooth.
Pour the wet mixture into the dry ingredients and stir until just combined with no large lumps remaining.
Divide the batter evenly among the four liners and bake for 18 to 20 minutes, until a toothpick inserted in the center comes out clean.
Let the cupcakes cool completely on a wire rack.
Use a small knife to cut a shallow cone out of the center of each cupcake and fill the hole with cherry pie filling.
In a chilled bowl, whip the heavy cream with the powdered sugar until soft peaks form.
Pipe or spoon the whipped cream over each cupcake and finish with dark chocolate shavings.