Preheat the oven to 425°F and line a baking sheet with parchment paper.
Place the acorn squash halves on the baking sheet cut-side up. Drizzle with olive oil, maple syrup, and sprinkle with salt and pepper. Use your hands to coat the squash. Sprinkle the sage and/or rosemary into the center of the squash and roast until tender and golden brown around the edges, 25 to 40 minutes depending on the size of your squash.
Season to taste and serve hot as a side dish, or pair it with herbed farro to make it a meal.
For an easy variation, you can roast the squash in slices instead of halves. Use the same method to season them, but cut the squash halves into 1/2-inch half-moons. Roast them until tender, for 25 to 30 minutes. I like to use this method when I add acorn squash to fall salads like this one.