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Preheat oven to 400 degrees. Line a a baking sheet with parchment paper or aluminum foil and set aside. Trim the stem ends of the Brussels sprouts and put into a medium bowl. Sprinkle with salt and pepper.
Cut the bacon in half and wrap each brussels sprout with bacon and secure with a toothpick. Lay them onto the baking sheet.
In a small bowl whisk together the maple syrup and brown sugar. Brush on top of the Brussels sprouts.
Bake for 30 minutes tossing them half way through until the bacon is crisp and Brussels sprouts are tender. Remove immediately from the baking sheet and place them on a serving dish.