Step 1: Preheat and Prep

Preheat your oven to 375°F (190°C). Line a large baking sheet with aluminum foil for easier cleanup. If you have one, place a wire rack on top of the foil—this allows grease to drip away and helps bacon crisp evenly on all sides. If using toothpicks, soak them in water for 10 minutes to prevent burning.

Step 2: Cut the Bacon

Lay out your bacon strips on a cutting board. Using a sharp knife or kitchen scissors, cut each bacon strip into 3 equal pieces. You should end up with about 36-40 pieces, which is perfect for wrapping all your smokies. Don’t worry about making them exactly even—close enough works fine!

Step 3: Wrap the Smokies

Take one piece of bacon and wrap it around one little smokie, starting at one end and wrapping in a spiral until the smokie is covered. The bacon piece should wrap around once or slightly more. Secure the bacon by inserting a toothpick through the bacon and smokie—this holds everything together during baking. Place the wrapped smokie on your prepared baking sheet. Repeat with remaining bacon and smokies, arranging them in a single layer with a bit of space between each.

Step 4: Add the Brown Sugar

Once all smokies are wrapped and on the baking sheet, generously sprinkle brown sugar over each one. Don’t be shy—you want a good coating of sugar on top of each bacon-wrapped smokie. The sugar will melt and caramelize during baking, creating that delicious sweet glaze. If making spicy version, mix red pepper flakes or cayenne with the brown sugar before sprinkling.

Step 5: Bake

Place the baking sheet in your preheated oven and bake for 25-30 minutes. Check at 20 minutes—the bacon should be crispy and golden brown, the sugar should be caramelized and bubbling, and the smokies should be heated through. If bacon isn’t crispy enough, bake for an additional 5-10 minutes, watching to prevent burning.

Step 6: Drain and Cool Slightly

Remove from oven and let cool for 2-3 minutes. If there’s excess grease pooled on the baking sheet and you didn’t use a wire rack, carefully transfer smokies to a paper towel-lined plate to drain briefly, then move to your serving platter. Be careful—they’re very hot and the caramelized sugar is molten!

Step 7: Serve

Transfer bacon wrapped smokies to a serving platter. Serve warm with toothpicks already inserted for easy grabbing. Provide a small bowl for used toothpicks. Watch them disappear within minutes!