Gather all ingredients.
Preheat the oven to 325 degrees F (165 degrees C). Line a large, rimmed baking sheet with parchment paper or aluminum foil.
Wrap each cocktail wiener with a piece of bacon; secure with a toothpick. Place bacon-wrapped wieners on the prepared baking sheet.
Evenly sprinkle brown sugar over the tops of the bacon-wrapped wieners.
Bake in the preheated oven until bacon is crisp and sugar is bubbly, about 40 minutes.
Serve immediately, or place in a slow cooker set on Low to keep warm.
