Remove the seeds and brush the insides of the acorn squash with 1 tbsp olive oil.
Sprinkle ½ tsp salt and ½ black pepper across the insides of the acorn squash.
Place the squash cut side down on a foil or parchment lined baking sheet.
Place in the oven to roast for 30 minutes.
On another baking sheet, lined with foil, spread the brussels sprouts out in an even layer
Add the garlic, pancetta and cranberries.
Drizzle with the additional 2 tablespoons of olive oil and the balsamic vinegar.
Sprinkle the remaining ½ tsp salt and ½ tsp black pepper on the brussels sprouts and toss everything together.
Place in the oven with the squash for 20-25 minutes.
Fill each half of squash with the roasted brussels sprouts and serve.
Notes
Vegetarian Option: Omit the pancetta to make this recipe vegetarian, and vegan.
Pancetta substitution: diced thick cut bacon can be used instead of the diced pancetta.
Cranberry substitution: dried cranberries can be substituted for fresh cranberries. They should be added to the brussels sprout filling after it's roasted. Frozen cranberries can be used in place of fresh cranberries with no change to the roasting time.