Pre-heat the oven to 450°F.
Place bacon on a foil lined baking sheet and bake for 35 – 45 minutes or until crisp.
Remove the bacon to a paper towel-lined plate and leave a tablespoon or so of the bacon drippings in the pan.
Place the butternut squash cubes and halved Brussels sprouts in a bowl.
Drizzle 2 tbsp. olive oil and 1/2 tsp. ground cinnamon over the vegetables; toss until evenly coated..
Transfer to a baking sheet and spread the vegetables in a single layer; season with salt and pepper to taste; toss with the bacon drippings if using.
To get a beautiful caramelization on the Brussel sprouts, flip them cut side down.
Roast the vegetables in the pre-heated oven for 20 to 30 minutes; this will vary depending on the size of the Brussels sprouts and butternut squash cubes.
Toss gently a couple of times during the cooking process.
During the last 5 minutes of cooking, drizzle 3 tablespoons maple syrup over the vegetables, and add the dried cranberries; toss gently to coat.
Remove from the oven and add cooked and crumbled bacon and toasted pecans before serving.
Pre-heat oven to 400°F.
Halve the butternut squash, peel, and cut into into 1/2-inch pieces.
Halve or quarter the brussels sprouts, lengthwise.
In a large bowl, mix Brussels sprouts, squash, and cranberries.
Drizzle oil and maple syrup over top; stir well.
Place mixture into two large baking sheets and place in the oven; layering the vegetables in one pan, will increase cooking time and texture may be compromised.
Lightly sprinkle with salt and pepper.
Place in oven and bake 35 – 45 minutes, stirring occasionally.
