Preheat the oven to 400 degrees Fahrenheit. Line a baking sheet with parchment paper or aluminum foil and set aside.
Trim the stem ends of 1 pound Brussels sprouts and add them to a medium bowl. Toss them with 1 tablespoon olive oil, salt, and ground black pepper to taste.
Wrap each Brussels sprout with a half slice of the 1 pound bacon cut in half, and secure with a toothpick, if necessary. Lay them on the baking sheet so they don’t touch each other.
Whisk together ½ cup real maple syrup and 3 tablespoons packed brown sugar in a small bowl. Use a pastry brush to brush this over the tops of the Brussels sprouts.
Bake for 30 minutes, flipping them halfway through, until the bacon is crisp and the Brussels sprouts are tender. Remove immediately from the baking sheet and place them on a serving dish. Serve warm with your favorite creamy dip.
Video
Notes
Make Ahead, Storage & Reheating Instructions
Prepare Ahead: Wrap sprouts and make the glaze up to a day in advance. Store in an airtight container in the fridge for 2–3 days before baking.
Storage: Keep leftovers in an airtight container in the fridge for up to 5 days.
Reheating: Reheat in the air fryer at 375°F or in the oven at 400°F for 5–10 minutes.