How to Make It
Cook bacon in a large skillet over medium until crispy, 4 to 5 minutes per side. Transfer to a plate lined with a paper towel. Break into bite-sized pieces.
Combine brown sugar, butter, and milk in a medium saucepan over medium-high. Bring to a boil, and cook, stirring often, until sugar is dissolved, about 2 minutes. Remove from heat, and stir in bourbon. Set aside.
Use toothpicks to hold doughnut holes onto Styrofoam cone, starting at the base and building to the top, placing one doughnut at the tiptop. Place bacon in gaps between the doughnuts. Drizzle caramel sauce over doughnut cone. Dust with powdered sugar. Serve immediately or at room temperature.