Preheat the oven to 400 degrees.
Slice the acorn squash in half lengthwise. If you’re cutting the stem of the acorn squash in half, you’re doing it correctly. Scoop out the seeds on the inside. Place the acorn squash halves on a baking sheet lined with parchment paper. Brush the olive oil on the flesh of the acorn squash, then season with extra salt and pepper.
Place the cut side down on the parchment paper (skin facing up), then place the baking sheet in the oven.
Bake for 30 minutes, until the flesh is tender.
Meanwhile, in a large skillet, heat up 1 tablespoon of olive oil over medium-low heat. Add the shallot, minced garlic, celery, salt, pepper, rosemary, and sage. Cook for 3-5 minutes or until the veggies become soft.
Add the diced chicken sausage. Stir and cook until the chicken sausage and cook for another 3-4 minutes.
Add the diced apple. Cook for another 1-2 minutes, or until the apple becomes soft.
Turn off the heat. Add in the dried cranberries, grated parmesan cheese, and breadcrumbs. Stir to combine.
Flip the cooked acorn squash halves over. Stuff each half with the stuffing mixture.
Pour the chicken broth over the stuffing evenly between the two halves.
Bake in the oven for another 15 minutes.