Step 1: Preheat your oven to 400°F (200°C). Line a large baking sheet with parchment paper for easy cleanup.
Step 2: Carefully cut the acorn squash in half lengthwise. Use a sturdy spoon to scoop out all the seeds and fibrous strands from both halves.
Step 3: Place the squash halves cut-side down on a cutting board. Carefully slice each half into 1/2-inch thick crescent-shaped slices.
Step 4: In a large mixing bowl, combine the acorn squash slices with olive oil, salt, and black pepper. Toss gently until all the squash pieces are evenly coated.
Step 5: Arrange the seasoned squash slices in a single layer on the prepared baking sheet, ensuring they are not overlapping. Roast in the preheated oven for 20 minutes.
Step 6: Remove the baking sheet from the oven. Drizzle the honey evenly over all the squash slices. Gently toss to coat the squash. Return to the oven and roast for another 10-15 minutes, or until the squash is tender and lightly caramelized.
Step 7: While the squash finishes roasting, prepare the cranberry drizzle. In a small saucepan, combine the cranberries, water, and granulated sugar. Bring the mixture to a simmer over medium heat, stirring occasionally. Cook for about 5-7 minutes, or until the cranberries burst and the sauce thickens slightly. If desired, stir in the orange zest. Remove from heat.
Step 8: Once the squash is tender and beautifully glazed, remove it from the oven. Carefully transfer and arrange the warm squash slices on a serving platter.
Step 9: Evenly sprinkle the crumbled goat cheese over the warm acorn squash slices.
Step 10: Spoon the warm cranberry drizzle over the squash and goat cheese just before serving. Serve immediately and enjoy!