Prepare the candied bacon first. Preheat your oven to 375°F (190°C). Line a baking sheet with parchment paper or aluminum foil and place a wire rack on top. Lay bacon strips on the rack, ensuring they don’t overlap.
Create the bacon glaze. In a small bowl, mix brown sugar and 2 tablespoons maple syrup. Brush this mixture onto both sides of the bacon strips.
Bake the bacon until crispy and caramelized, about 20-25 minutes. Watch carefully after 15 minutes as the sugar can burn quickly. Once done, remove from oven and let cool completely before chopping three-quarters into small pieces, reserving the rest for garnish.
Reduce oven temperature to 350°F (175°C) and line a 12-cup muffin tin with cupcake liners.
Combine the dry ingredients by whisking together flour, baking powder, and salt in a medium bowl. Set aside.
Cream butter and sugar in a large bowl using an electric mixer on medium-high speed until light and fluffy, about 2-3 minutes.
Add eggs one at a time, beating well after each addition. Mix in the 1/2 cup maple syrup and vanilla extract until fully incorporated.
Alternate adding the dry ingredients and milk to the butter mixture, beginning and ending with the dry ingredients (three additions of dry, two of milk). Mix on low speed just until combined.
Fold in the chopped candied bacon pieces gently with a spatula until evenly distributed.
Fill each cupcake liner about 2/3 full with batter. Don’t overfill or they’ll overflow during baking.
Bake for 18-20 minutes or until a toothpick inserted into the center comes out clean with just a few moist crumbs.
Let cupcakes cool in the pan for 5 minutes before transferring to a wire rack to cool completely.
Prepare the frosting by beating butter until creamy. Gradually add powdered sugar, maple syrup, maple extract (if using), and salt. Beat on medium-high speed until light and fluffy, about 3-4 minutes.
Frost the completely cooled cupcakes using a piping bag or offset spatula. Top each cupcake with a piece of the reserved candied bacon.