1. Preheat oven to 400°F.
2. Place cut acorn squash, Brussels sprout halves, and pecans in a large bowl. In a separate small bowl, mix maple syrup and brown sugar.
3. Pour the olive oil on the vegetables, stir well, add maple syrup mixture and mix until all the ingredients are well coated. Add olive oil if the mixture looks dry. Season with salt and pepper.
4. Line a large baking pan with two layers of aluminum foil. Place the vegetables on the pan, and arrange them in a single layer. Roast 35-40 minutes until vegetables are tender. Take the pan out of the oven, add bacon pieces, gently toss to combine, return to the oven for another 5-8 minutes.
5. Serve immediately.