Preheat oven to 400°F (200°C).
Line a baking sheet with parchment paper.
Wash and peel the winter squash.
Cut squash into thick wedges.
Place wedges in a large mixing bowl.
Drizzle olive oil over the wedges.
Add salt, pepper, and spices.
Toss until all wedges are coated evenly.
Arrange wedges on the baking sheet.
Spread them in a single layer.
Roast for 25 minutes on one side.
Flip wedges halfway through roasting.
Continue roasting for 15 more minutes.
Check for crisp edges and tender flesh.
Remove from oven and let cool slightly.
Sprinkle Parmesan if desired before serving.