Preheat your oven to 400°F (200°C).
Carefully cut each acorn squash in half lengthwise using a sharp knife. Scoop out the seeds and stringy pulp with a spoon.
In a mixing bowl, combine the maple syrup, olive oil, cinnamon, and a pinch of salt and pepper.
Brush the mixture generously over the cut sides of the acorn squash halves.
Place the squash halves, cut side up, on a baking sheet. Sprinkle the chopped pecans over each half.
If desired, cover the baking sheet with aluminum foil to help steam the squash for the first 20 minutes of cooking.
Roast the squash in the preheated oven for 25 minutes, then remove the foil (if used) and roast for an additional 20 minutes, or until the squash is tender and caramelized.
Remove from the oven and let it cool for a few minutes before serving.