Preheat oven to 350 degrees. Insert paper liners into the cups of 2 standard muffin pans.
In the bowl of an electric mixer, preferably fitted with a paddle attachment, cream the butter and sugar on medium speed until very light and fluffy, about 5 minutes. Turn mixer to low and add the eggs, one at a time until each egg is fully mixed in, scraping down the sides of the bowl with each addition. Add the vanilla extract and mix well.
In a separate large mixing bowl, whisk together the flour, cocoa powder, baking powder and salt.
With the mixer on low, add the flour mixture and milk to the creamed butter, starting with 1/3 of the flour mixture, then half the milk, half the remaining flour mixture, the rest of the milk and the rest of the flour mixture. Mix until just combined. Remove bowl from mixer and scrape the sides and bottom of the bowl well with a large spatula.
Spoon 2 tablespoons of batter into each prepared muffin cup, add 3 of the red tart cherries to each cup then top with 2 more tablespoons of batter. Bake for 20 - 25 minutes or until springy on the top. Allow to cool in pan for about 5 minutes.
With a toothpick, poke 6 or 8 holes in each cupcake. Spoon about 1 teaspoon of reserved maraschino cherry liquid onto each cupcake and let it soak in. Remove cupcakes to a wire rack to cool completely.
Whip cream in a large bowl until soft peaks form. Add the confectioners’ sugar, vanilla and 1 tablespoon of reserved maraschino cherry juice. Beat until stiff.
Frost cupcakes and garnish with a maraschino cherry and some grated chocolate.