Preheat your oven to 400°F (200°C). In a large mixing bowl, toss halved Brussels sprouts with olive oil until evenly coated.
Spread the oiled Brussels sprouts onto a baking sheet in a single layer, ensuring they aren’t overcrowded to promote even roasting.
Place the baking sheet into the oven and roast for about 20-25 minutes, shaking the pan halfway through, until the sprouts are tender and charred at the edges.
While the sprouts are roasting, cook the bacon in a skillet over medium heat until crispy. Drain on paper towels and then chop into small bits.
Once out of the oven, drizzle the maple syrup over the roasted Brussels sprouts, and gently toss to coat evenly in the glossy glaze.
Sprinkle the crispy bacon bits over the glazed Brussels sprouts, then season with salt and freshly ground pepper to taste.
Serve immediately, allowing the flavors to meld and the dish to retain its appealing glisten and crispy textures.