Preheat the oven to 400°F (200°C).
Cut the acorn squashes in half and remove seeds.
Drizzle olive oil over the cut sides and season with salt and pepper.
Place the squashes cut-side down on a baking sheet.
Roast in the oven for 25–30 minutes, until tender.
While the squash roasts, prepare the honey glaze by combining honey and thyme (if using) in a small bowl.
Once the squash is tender, remove it from the oven and carefully flip each half cut-side up.
Brush the honey glaze over the cut surfaces of the squash.
Return the squash to the oven and roast for an additional 10 minutes until the glaze is bubbly and caramelized.
Meanwhile, prepare the cranberry drizzle by simmering cranberries with a tablespoon of water in a small saucepan until they burst.
Remove the pan from heat and let cranberries cool for a few minutes, then mash gently with a fork.
Serve the roasted squash topped with crumbled goat cheese and the cranberry drizzle.
