Stuffed Acorn Squash

Stuffed acorn squash is an autumnal delight! Italian sausage, cranberries, spinach,  sage, and rosemary are stuffed into acorn squash, sprinkled with parmesan cheese, and roasted until tender and bubbling. This gluten free and paleo friendly recipe is a crowd-pleasing stunner. 

I’m thrilled to round out that list today with sausage stuffed acorn squash. It’s sweet, it’s savory, it’s cute. Like big cozy sweaters, wood burning stoves, and spiced apple cider, stuffed acorn squash is cozy, delightful, and oh so perfectly autumn!

HOW TO MAKE STUFFED ACORN SQUASH

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.

ROAST THE ACORN SQUASH

To prepare the squash for roasting, start by trimming each end. Place the squash on its side and using a sharp knife trim off the top just below the stem. Then slice about half an inch off the bottom. Be careful not to trim too much or you’ll have a hole in the bottom of your squash (like the one I did below!). Lastly, slice the squash through the center to create two halves.

Place the squash cut side up on the cutting board and scoop out the seeds using a spoon. Acorn squash have soft flesh, so they’re quite easy to de-seed.

Drizzle each squash with olive oil, then dust with salt and pepper. Place the squash flesh side down onto a parchment lined baking sheet and roast in a 400°F oven until the flesh is soft and the skin can be easily pierced with the tip of a knife. Total cooking time will depend on the size of your squash, but start with 30 minutes.

MAKE THE SAUSAGE AND VEGETABLE STUFFING

While the squash is roasting you’ll make the stuffing. The stuffing preparation moves a little fast, so be sure to have your mise en place ready before you start (that’s just a fancy way of saying “have all your ingredients prepped and ready before you start cooking”).

Sautee a pound of mild italian sausage until it’s browned and cooked through. Break it up into small bits with a wooden spoon. Remove the sausage from the skillet with a slotted spoon, leaving the rendered fat behind.

Once the spinach has wilted, mix the contents of the skillet with the cooked sausage and stir it all together. Add some parmesan cheese if you want to rock the dairy train, or skip it to keep this paleo and dairy free.

STUFF AND REHEAT

By the time the stuffing is cooked, the squash should be ready. Remove it from the oven and flip over, being mindful of any steam that might escape.

Stuff each squash with a quarter of the sausage and vegetable stuffing. You’ll have quite a bit of stuffing, so go ahead and pile it on top pretty generously. Add the stuffed squash back to the oven and bake an additional 5 or so minutes, until the cheese has softened and the stuffing is bubbling.

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Stuffed Acorn Squash

Ingredients

2 acorn squash

1 tbsp olive oil

1/2 tsp sea or kosher salt

1/2 tsp cracked black pepper

1 lb italian sausage

1 leek halved and thinly sliced

1 rib celery thinly sliced

2 cloves garlic minced

1 tbsp chopped fresh sage

1 tbsp chopped fresh rosemary

1/2 c dried unsweetened cranberries

1 tbsp red wine vinegar

4 oz spinach chopped (or whole if using baby spinach)

1/2 c parmesan cheese optional

1 tbsp chopped parsley for garnish

Instructions

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.