Preheat oven to 350 degrees F. Line 28 muffin cups with paper liners.
Mix together the flour with the cocoa powder, baking soda, and salt.
Beat the butter with an electric mixer at medium speed until smooth, about 2 minutes. Increase the speed to medium-high and gradually add both sugars. Beat for about 3 minutes. Beat in the eggs, one at a time. Beat in the vanilla. Using lowest speed of mixer, add flour and milk alternately.
Divide the batter equally among the muffin cups (about 2/3 full) and bake until the centers of the cupcakes spring back when pressed gently, about 25 minutes. Cool on a rack for 10 minutes then remove from the tin and cool completely before frosting.
Frosting: Mix the butter and powdered sugar together in bowl of a stand mixer using low speed. Add a little of the milk to soften and continue beating until mixture comes together. Add vanilla. Add milk 1 tablespoon at a time until you get the consistency you want. Beat until light and fluffy. Add a drop or two of red food coloring.
Frost the cupcakes then decorate with chocolate sprinkles and stemmed cherries.