Cut the acorn squash in half, scoop out seeds and strands and place on a baking sheet, cut sides up.
Coat inside and cut edges of squash with olive oil and sprinkle generously with salt and pepper and place the cut sides down on the baking sheet.
Roast in the preheated oven for 30-45 minutes.
While the squash is roasting, remove the casings from the Italian sausage and add to a skillet.
Add chopped onions, garlic, diced peppers and Italian seasoning to the sausage and cook until sausage is browned and broken into crumbles.
Add chopped pecans and dried cranberries to a small mixing bowl and stir in the sausage mixture.
When squash are roasted, remove from the oven and turn squash cut side up to add the filling. Add filling to each squash.Reduce oven to 350° and return the filled squash to the oven for an additional 20-30 minutes, being careful not to burn the filling.
While squash are roasting, mix together brown sugar and cinnamon in a small bowl.
Remove roasted squash from oven and serve immediately. Sprinkle squash with the brown sugar and cinnamon mixture to make the flavor over the top!
Refrigerate leftovers in an airtight container in the fridge for up to 4 days. Reheat the squash in a preheated 350° oven for about 30 minutes or until heated through. Feel free to stir filling before reheating leftovers to ensure it doesn't over brown. Add brown sugar topping when serving.
Notes
A great roasted acorn squash filled with savory Italian sausage stuffing and topped with brown sugar and cinnamon for the best fall flavor!Enjoy!
Keyword great acorn squash side dish, great lunch main dish stuffed acorn squash, Stuffed Acorn Squash, Sweet & Savory Acorn Squash, Sweet & Savory Stuffed Acorn Squash