Preheat the oven to 425°F and line a large baking sheet with parchment paper.
Place the acorn squash halves on the baking sheet cut side up.
In a small bowl, combine the olive oil and maple syrup and whisk until thick and smooth. Brush about half onto the cut sides of the acorn squash, using just enough to lightly coat the squash. Sprinkle with salt and pepper and rub with your hands to coat. Place the squash cut side down and roast for 20 to 30 minutes, or until caramelized around the edges.
Remove from the oven and flip the squash halves cut side up. Brush with the remaining maple mixture. Sprinkle with the herbs, if using. Return to the oven and roast, cut side up, for 10 to 15 more minutes, or until completely tender.