Preheat oven to 400°F (200°C). Brush squash halves with olive oil and season with salt and pepper. Place cut-side down on a baking sheet and roast for 25-30 minutes until tender.
Flip squash halves cut-side up. Drizzle with honey and return to oven for 5 minutes until glazed and caramelized.
Meanwhile, in a small saucepan, combine cranberries, orange juice, maple syrup, and cinnamon. Simmer over medium heat until cranberries burst and sauce thickens, about 8-10 minutes.
Fill each squash half with crumbled goat cheese. Drizzle with cranberry sauce and garnish with fresh thyme before serving.
