Stuffed acorn squash is easy to prepare and presents beautifully, but it does take about an hour start to finish, so leave this for weekends if you're pressed for time. Fresh herbs are the key to making the stuffing really pop, so don't substitute for dried if you can help it.
4ozspinachchopped (or whole if using baby spinach)
1tbspchopped parsleyfor garnish
Heat the oven to 400°F. Line a baking sheet with parchment paper.
Trim both the tops and bottoms of the acorn squash. Slice each squash in half widthwise and scoop out seeds. Drizzle each squash half with a scant teaspoon olive oil, then rub the oil all over the squash including the flesh and skin. Sprinkle the flesh with salt and pepper. Place the squash cut side down onto the prepared baking sheet and place in the oven. Roast until tender, and the skin can be easily pierced with the tip of a knife, 30-35 minutes.
While the acorn squash is roasting, prepare the the stuffing. Heat a 10” cast iron skillet oven medium high heat. Add the sausage and cook, stirring frequently to break it up, until the sausage is crispy and no longer pink, 7-8 minutes. Remove the sausage using a slotted spoon and place into a mixing bowl.
Add the leeks and celery to the skillet and sautee in the rendered sausage fat until soft, 6-8 minutes.
Add the garlic and sautee, stirring frequently, until fragrant, about 1 minute.
Add the herbs and cranberries, stir to combine with the vegetables, and sautee an additional 2 minutes until very fragrant.
Add the vinegar to the skillet to deglaze, scraping up any browned bits from the bottom. Add the spinach and sautee, tossing continuously, until wilted.
Transfer the sautéed vegetables to the bowl with the sausage, then add the parmesan cheese if using. Toss until evenly distributed.
Remove the squash from the oven. Using tongs, flip over each squash half, being careful of any steam that may have built up.
Fill each squash with a quarter of the sausage and vegetable stuffing. Return the stuffed squash to the oven and bake an additional 5 minutes, or until the cheese is melted and the stuffing is bubbling.
Remove from the oven, sprinkle with chopped parsley serve immediately.