Preheat the oven to 400 degrees F and line a baking sheet with parchment paper.
In a large bowl, combine the Brussels sprouts with 1 tablespoon of the olive oil, the salt, pepper, and garlic powder.
Place the Brussels sprouts on the parchment-lined baking sheet and bake for 25 to 30 minutes, until fork-tender.
While the sprouts are baking, cook the bacon in a large saute pan over medium heat until crispy, then remove to a plate lined with paper towels to drain. When cool, chop into small pieces. Drain most of the bacon fat from the pan, leaving a little to grease the bottom of the pan.
When the Brussels sprouts are done, return the saute pan with the bacon fat to medium heat and add the remaining tablespoon of olive oil. When the oil is hot, add the baked Brussels sprouts to the pan.
Pour 1 tablespoon of maple syrup over the Brussels sprouts and toss to coat evenly with a wooden spoon.
Cook over medium heat for 5 minutes, stirring often, until the sprouts are well coated and the maple syrup starts to caramelize them. Remove from the heat and sprinkle with the bacon. Taste, season with additional salt and another tablespoon of maple syrup, if desired, and mix to incorporate. Serve immediately.