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Stuffed Roasted Acorn Squash With Italian Sausage And Pears


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My favorite part of any stuffing is the crunchy and caramelized topping that occurs in the last minutes of cooking. How the croutons become golden brown, the pears release their sugars and glisten from that slight char and the crunchy exterior of the sweet Italian sausage. Yet inside, the stuffing is soft and flavorful. What I’m describing is my Stuffed Roasted Acorn Squash With Italian Sausage And Pears.

Let me start by telling you how by roasting these beautiful winter squash I bring their flavor before filling them with savory sausage and sweet pears.

Here I have two types of acorn squash. I cut the tops off first, then remove the all the seeds carefully not to dig too far in and disrupt the inside bottom of the squash. Cut a small slice off the bottom. You want the squashes to sit upright while roasting.

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For the veggies and herbs, I have diced cremini mushrooms, zucchini, celery, onions, Bosc pears, minced garlic, and chopped fresh sage. It’s important that all the veggies are relatively cut the same size. This way they will cook and be done at the same time.

In a large saute pan, on medium heat,  I have two tablespoons of butter along with a tablespoon of olive oil. Once that’s melted I add in the chopped sage leaves. This allows them to release their oils and perfume the butter and oil. Once you start to smell the sage it’s ready to add in the other ingredients.

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I then toss in all the veggies, with a tablespoon of Kosher salt and a teaspoon of black pepper. I let them saute, on medium-high heat long enough to get some color on them. This should only take about 5 to 7 minutes. As the veggies are sauteing, I work on cutting up 1/2 a loaf of Ciabatta bread into cubes. The cubes are about 1-1/2 inches in size. Because I got a head start roasting the acorn squash, this allowed the oven to be freed up.

Now that the oven has been freed up and the acorn squash is resting on the sidelines. the sausage has been cooked. The veggies are sauteing on the stove. The Ciabatta has been cubed up and the temperature to the oven is still at 400 degrees F. Drizzle some olive oil all over the top, with a sprinkling of Kosher salt and black pepper. Spread them out in a single layer onto two baking sheets. Place them into the oven a bake for about 10 minutes. Keep an eye on them. You just want them to be a light golden brown.

Once all the veggies have sauteed, I add the sausage to the veggies with some chili powder and the diced pears. I saute this for just a couple of minutes together allowing the flavors to marry. About 3 to 5 minutes more.

At this point, I transfer all the ingredients to a bowl and add some Parmigiano- Reggiano cheese and the baked croutons. I gently give all this a toss to combine. Now both squashes are ready to be stuffed.

One final step. They get a drizzle of olive oil over the top of each one and go back into the 400-degree oven for 3 to 5 minutes. Just long enough to get the tops golden brown and caramelized.

I know it’s a few steps to pull this dish together. Really all the steps are easy. It’s just a matter of having all the prep done and roasting the acorn squash first. I’ll explain in more detail in the directions at the end.

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Prep Time: 25 minutes
Cooking Time: 45 to 50 minutes
Total Time: 1 hour 15 minutes
Yields: 4 servings
Equipment: 12-inch sauté pan, 4 rimmed baking sheet pans, Chef’s knife, small mixing bowl, whisk, pastry brush

4 acorn squash that has been seeded and tops and bottoms cut
1 tablespoon Kosher salt
1 teaspoon black pepper
4 tablespoons of olive oil
1 stick of unsalted butter, melted
1 teaspoon of chili powder
1/4 cup of dark brown sugar

1 pound sweet Italian sausage, bulk or casings removed
1 tablespoon of chopped fresh sage leaves
2 tablespoons of unsalted butter
1 tablespoon of olive oil
2 diced Bosc pears
1 diced zucchini
6 cremini mushrooms, diced
1/2 onion, diced
3 cloves minced garlic
2 ribs of diced celery
1 tablespoon of Kosher salt
1 teaspoon of black pepper
1 tablespoon of chili powder
1/2 cup of grated Parmigiano-Reggiano cheese
3 heaping cups of  Ciabatta croutons, 1 /1/2 inch dice

Preheat oven to 400-degrees F.
Start by cutting the tops off the 4 squash. Next, clean the seeds out of the inside. Then cut a thin slice off the bottom of each one so they will sit upright on the baking sheets. Place 2 on each sheet tray. On the inside of each acorn squash add olive oil, Kosher salt, and fresh ground black pepper.

Bake for 30 to 35 minutes or until fork-tender. In a small mixing bowl with melted butter add chili powder and brown sugar, whisk to combine. Brush the inside of each squash with the flavored butter mixture and return to oven for another 5 to 7 minutes. Be sure to keep a close eye on the squash for the last few minutes of cooking. You don’t want them to burn. Remove the squash from the oven and allow them rest for 5 minutes before adding the stuffing.

For the stuffing, I’m starting by browning off skinless sweet Italian sausage. I break up the sausage with the back of a wooden spoon. With the stove on medium-high heat, I let the sausage saute until it is fully cooked. I want it to be brown and crumbly. This takes about 15 minutes. then I place the cooked sausage on a plate lined with a paper towel so it will be able to drain off any excess fat. While this is happening I start working on chopping the veggies up that will be going into the stuffing.



After the squashes are in the oven, brown off the sausage. The sausage takes about 15 minutes to be fully cooked and crumbly. While the that’s happening, chop the veggies for the stuffing. Transfer the sausage to a plate lined with a paper towel and set aside.

At this point, set the stove to medium heat, add the butter, olive oil, and chopped sage leaves to a large saute pan. Start sauteing the veggies with the chili powder, salt, and pepper. Once the veggies have started to soften, then add in the diced pears. This should take 5 to 7 minutes.

As the veggies are sauteing, cube up half the loaf of Ciabatta bread. Place them on two baking sheets. Drizzle them with olive oil, and sprinkle with Kosher salt and black pepper.

Transfer the cooked sausage and veggies to a large bowl. To the bowl add in the grated Parmigiano-Reggiano cheese. Remove the squash from the oven and place the bread cubes in at the same temperature for another 10 minutes. Keep an eye on them so they don’t burn. You just want crunchy golden croutons.

Once they come out of the oven, add them to the bowl with the other ingredients. Gently toss everything together and fill the acorn squash with the stuffing. I usually have a little leftover, that I place into a small ceramic dish. It can go into the oven with the squash. Place everything back into the 400-degree oven for about 3 to 5 minutes, until the tops are a nice golden brown.

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