Preheat oven: Set oven to 400°F (200°C) and line a baking sheet with parchment paper.
Cut squash: Slice each acorn squash in half lengthwise and remove the seeds and stringy pulp.
Slice or keep halves: You can roast them as halves or cut into 1-inch wedges for quicker cooking.
Season: Brush with olive oil or butter, drizzle with maple syrup, and sprinkle with salt, pepper, and cinnamon if desired.
Roast: Place cut side down on the baking sheet. Roast for 25–35 minutes, flipping halfway through, until tender and caramelized.
Serve: Garnish with fresh herbs and an optional drizzle of maple syrup before serving.