Step 1

Preheat oven to 400 degrees F.

Step 2

Using a sharp chef's knife, carefully cut the acorn squash in half. Cut a flat spot on the bottom so the acorn squash does not roll around while roasting. Using a spoon, scoop out the seeds and stringy pulp, discard. Careful not to scoop too far through the bottom or it will cause a hole and the stuffing will later fall out.

Step 3

Brush olive oil evenly onto the squash. Sprinkle a pinch of kosher salt and black pepper onto each squash to season.

Step 4

Roast for 30 minutes until you can just pierce with a fork (it will be going back into the oven with the stuffing to finish cooking through). [see note]

Step 5

While the acorn squash is roasting, in a dutch oven over medium/high heat, add in the 3 tbsp of olive oil and the Italian sausage. Fully cook the sausage through, about 8 minutes. Using a slotted spoon, remove the sausage and leave the oils/small bits in the pan. Set the sausage aside.

Step 6

Lower the heat to medium, add in the diced onion and celery, sauté for 4 minutes until they begin to soften. Add in the apples, sage, thyme, garlic, a pinch of kosher salt, fresh ground black pepper, and crushed red pepper flakes. Sauté for 4 minutes. Return the sausage back into the dutch oven with the vegetables and stir to combine. Allow flavors to meld for 3 minutes.

Step 7

Using a spoon, evenly add the stuffing into the acorn squashes.

Step 8

In a small bowl, mix together the panko bread crumbs and parmesan cheese. Sprinkle over the top of each acorn squash.

Step 9

Place the stuffed squashes into the oven for 15 minutes. The breadcrumbs/parmesan should be toasted brown. Remove from the oven and serve.