Preheat your oven to 400°F (200°C). Line a large baking sheet with parchment paper or silicone baking mats to prevent sticking and make cleanup easier.
Place the squash on a stable cutting board. Carefully cut off the stem and the very bottom. Cut the squash in half lengthwise from top to bottom. Use a metal spoon to scoop out the seeds and the stringy pulp from the center.
Slice each half into 1-inch thick wedges or rings. Keeping the slices uniform ensures that they all cook at the same rate. You do not need to peel the squash, as the skin becomes tender and edible after roasting.
In a large mixing bowl, toss the squash wedges with olive oil, maple syrup, cinnamon, salt, and pepper. Ensure every piece is evenly coated with the oil and seasonings for maximum flavor.
Arrange the squash wedges in a single layer on the prepared baking sheet. Avoid overcrowding the pan so the air can circulate. Roast for 25 to 30 minutes, flipping the wedges halfway through, until they are fork-tender and the edges are nicely browned.