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

Let me start by showing you how roasting winter squashes brings out their flavor. Then I’m going to go a step further and fill them with savory sausage and sweet pears.

Prep Time: 25 minutes
Cooking Time: 1 hour 30 minutes
Total Time: 1 hour 55 minutes
Yields: 4 servings
Equipment: 1 (12-inch) non-stick sauté pan, 4 rimmed baking sheet pans (1/4 size), chef’s knife, cutting board, 1 small mixing bowl, whisk, pastry brush

Ingredients for the Roasted Acorn Squash Stuffed With Italian Sausage And Pears:
4 acorn squash, seeded, and tops and bottoms cut
1 tablespoon kosher salt
1 teaspoon of black pepper, freshly-ground
4 tablespoons of olive oil
8 tablespoons (1 stick) of butter, unsalted and melted
1 teaspoon of chili powder
1/4 cup of light brown sugar

Ingredients for the Acorn Squash Stuffing:
4 prepared acorn squash
1 pound of sweet Italian sausage, bulk or casings removed
1 sprig plus 1 tablespoon of fresh sage leaves, julienned
2 tablespoons of butter, unsalted
1 tablespoon of olive oil
2 Bosc pears, diced
1 zucchini, diced
6 cremini mushrooms, diced
1/2 onion, diced
3 cloves garlic, minced
2 ribs of celery, diced
1 tablespoon of kosher salt
1 teaspoon of black pepper, freshly-ground
1 tablespoon of chili powder
3 heaping cups of Homemade Ciabatta Croutons, 1 /1/2 inch bread cubes
1/2 cup of Pecorino Romano cheese, freshly-grated
Garnishes:
Bib (Boston lettuce) lettuce
Fresh sage leaves

Instructions for the Homemade Ciabatta Croutons:
Preheat oven to 350°F.
Start by evenly dividing the bread cubes out onto two rimmed baking sheet pans. Add olive oil, kosher salt, and fresh-ground black pepper, and toss to coat. Spread the bread cubes evenly into a single layer. Bake for 15 minutes, turning them once halfway through to ensure they brown evenly.  Leave on sheet pans to cool.

Instructions for the Roasted Acorn Squash Stuffed With Italian Sausage And Pears:
Preheat oven to 400°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 30-35 minutes or until fork-tender. Melt the butter, then transfer it to a small mixing bowl. Add chili powder and brown sugar, and whisk to combine. Brush the inside of each squash with the flavored butter mixture. Return to the oven for another 5-7 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. Set aside.

In a large non-stick sauté pan over medium-high heat (no oil needed), add the skinless sweet Italian sausage. Using a wooden spoon, start breaking up the sausage. Cook the sausage for 15 minutes until brown, crumbly, and no pink remains. Transfer the cooked sausage to a plate lined with paper towels to drain the fat, then set aside.

Tip: Take a paper towel and wipe out the sauté pan. No reason to dirty another pan.

Using the same sauté pan over medium heat, melt butter, olive oil, and chopped sage leaves. Once the sage becomes fragrant, add the diced cremini mushrooms, zucchini, celery, onions, Bosc pears, minced garlic, chili powder, kosher salt, and fresh-ground black pepper. Once the veggies start to soften, add in the diced pears. Stir and continue to cook for 5-7 minutes. Add the cooked sausage back to the pan, and stir to combine. Cook for an additional 3-5 minutes. Turn off the heat.

At this point, add the sausage and vegetable mixture to the bowl with the croutons. Add the grated Pecorino Romano cheese, and gently toss to combine.

Fill each of the squashes with the filling. Any extra filling is placed into an oven-safe baking dish. Drizzle olive oil over the top of each one and place back into the oven for 3-5 minutes or until the tops become golden brown and caramelized.

First, place the leafy greens on the plate. Arrange the Roasted Acorn Squash Stuffed With Italian Sausage And Pears on top. Garnish with a sprig of fresh sage. Serve hot.

There you have it, my Roasted Acorn Squash Stuffed With Italian Sausage And Pears.

Note:
1) All the veggies must be relatively cut the same size, ensuring they’ll cook at the same time.

2) Linda Lou Hamel is not a nutritionist or dietitian, and any nutritional information shared is an estimate. If calorie count and nutritional value are important to you, I recommend running the ingredients through the online nutritional calculator of your choice. Calories and values can vary depending on the brands you choose.

https://lindalouhamel.com/2019/07/10/summer-time-flowers-and-herbs/

https://lindalouhamel.com/2015/11/02/homemade-ciabatta-croutons/