Start by preheating your oven to 325 degrees and line a muffin tin with cupcake liners.
Adding your flour, sugar, cocoa powder, baking powder, baking soda, salt and espresso powder to a large mixing bowl. Stir the dry ingredients around to combine them and then add in the milk, vegetable oil, eggs, vanilla, bourbon and hot water. Mix to combine for 1 - 2 minutes and then spoon batter into your cupcake tins, careful to fill cupcake liners only about half way up.
Bake for 19-22 minutes, remove Chocolate Bourbon Maple Bacon Cupcakes from the muffin tin and move to a cooling rack.
While your cupcakes are cooling, cook off the bacon in a large skillet over medium high heat. Once bacon is cooked crisp, move bacon to a paper towel to drain the grease. Once the bacon is cool to touch, dice up and set aside.
When cupcakes are completely cool, make your Maple Bourbon Buttercream Frosting. Start by adding softened butter to a large mixing bowl and beating until creamy. Sift in the powdered sugar and salt, then add in the maple syrup and bourbon and mix to combine. If the frosting is too thin, add in more powdered sugar, if it is too thick, add a bit of milk to thin the frosting out. Frost your Chocolate Bourbon Maple Bacon Cupcakes and then using your fingers, lightly add the bacon pieces to the frosting and lightly press to make sure they stick.