Preheat the oven to 350°F (175°C).
Line a rimmed baking sheet with parchment paper. Place a wire cooling rack inside the lined pan.
Arrange the crackers in a single layer on the wire rack.
Wrap each cracker with half a slice of bacon.
In a small bowl, combine the brown sugar, black pepper, and cayenne pepper.
Generously sprinkle the sugar mixture over the top of each bacon-wrapped cracker.
Drizzle a small amount of maple syrup over each cracker, if using.
Bake for 25 to 35 minutes, or until the bacon is cooked and the sugar has melted and started bubbling.
Allow the crackers to cool on the rack for approximately 10 to 15 minutes before serving.