Preheat oven to 425°F.
Mix 1 tablespoon of the olive oil and the butternut squash in a small bowl until evenly coated.
Spread the squash onto one half of a baking sheet, season with 1/2 teaspoon salt and 1/4 teaspoon pepper, and sprinkle on the cinnamon.
Toss the Brussels sprouts with 1 tablespoon of the olive oil and spread them onto the other half of the baking sheet. Season with 1/2 teaspoon salt and 1/4 teaspoon pepper.
Roast until just caramelized, about 30 minutes, tossing every 10 minutes or so.
In a large, heavy-bottomed deep skillet (or Dutch oven) add 1 tablespoon of olive oil over medium heat. Add the garlic and cook for 1 minute.
Mix in the arborio rice and cook for an additional minute. Then, pour in the white wine. Cook until the wine is fully absorbed.
Add 3 cups of the stock one cup at a time, letting each cup absorb fully before adding the next.
Then, add the last cup of stock 1/4 cup at a time until rice is cooked as desired - creamy, yet still somewhat al dente.
Once all the stock is absorbed, remove the pan from heat and stir in the butter pieces, and Parmesan cheese until well blended.
Gently, fold in the roasted butternut squash.
Pour the Roasted Butternut Squash Risotto into a large serving bowl.
Top with the roasted Brussels sprouts, cranberries, and walnuts.