Preheat the oven to 350°F (175°C). Line a baking sheet with foil and lightly coat with nonstick spray.
Pat the little smokies dry with a paper towel.
Cut the bacon into thirds, then wrap each sausage with a piece of bacon. Secure with a toothpick.
Place the brown sugar in a large zip-top bag. Add a few bacon-wrapped smokies at a time, seal the bag, and shake to coat evenly. Repeat until all are coated.
Arrange the smokies on the prepared baking sheet in a single layer. Sprinkle with freshly ground black pepper, if desired.
Bake for 30–35 minutes or until the bacon is browned and crispy.
For extra crispiness, broil for 1–2 minutes, watching closely to prevent burning.
Remove from the oven and let cool for a few minutes before serving. Enjoy warm with your favorite dipping sauce!