Preheat your oven to 400°F.
In a large bowl, combine the trimmed Brussels sprouts, cubed butternut squash, and sliced shallots. Drizzle in the olive oil and toss until well coated.
Spread the vegetable mixture evenly onto a baking sheet. Season with salt, pepper, and cinnamon, then toss again.
Roast in the preheated oven for about 30 minutes, tossing halfway through.
In a small skillet, add walnut halves and maple syrup over medium-high heat. Stir for 2-4 minutes until syrup thickens and coats walnuts. Transfer to a plate to cool.
Mix in dried cranberries with the roasted vegetables and sprinkle crumbled goat cheese on top if desired.