Penne with Squash and Italian Chicken Sausage

Preheat oven to 400°F. Brush cut sides of squash with 1 tablespoon of the oil, and season evenly with pepper and ½ teaspoon of the salt. Place squash halves, cut side down, on a rimmed baking sheet lined with parchment paper. Roast until almost tender, about 30 minutes. Remove squash from oven; set aside until cool enough to handle, about 10 minutes. Using a spoon, scrape flesh from 2 squash halves into a medium bowl; discard skin. Add pan drippings from sheet pan. Cut remaining halves lengthwise into 2 equal pieces. Carefully cut away skin from flesh, and discard skin. Cut squash flesh into ½-inch cubes; set aside.

While squash roast, bring a large pot of salted water to a boil over high. Add pasta, and cook until very al dente (about 2 minutes shorter than package directions call for), and drain. Set aside.

Heat 1 tablespoon of the oil in a large deep nonstick skillet over medium-high. Add sausage. Cook, turning occasionally, until sausage is well browned and a thermometer inserted in sausage registers 165°F, about 10 minutes. Transfer sausage from skillet to a plate lined with paper towels. Add remaining ½ tablespoon oil to skillet. Add red bell pepper to skillet, and cook, stirring occasionally, until tender, about 5 minutes. Using a slotted spoon, transfer cooked red bell pepper to a medium bowl, and set aside; reserve drippings in skillet. Add yellow bell pepper and onion to skillet. Cook, stirring occasionally, until tender, about 5 minutes. Add garlic, thyme, and oregano. Cook, stirring constantly, until fragrant, about 1 minute. Add scraped squash flesh and pan drippings, chicken stock, and remaining 1 teaspoon salt to skillet, and bring to a boil over medium-high. Reduce heat to low. Simmer squash mixture, stirring occasionally, until thickened, about 15 minutes.

Working in batches if necessary, pour squash mixture into a blender. Secure lid on blender, and remove center piece to allow steam to escape. Place a clean towel over opening. Process until smooth, about 1 minute. Place squash puree back in deep skillet; whisk in heavy cream, and bring to a simmer over low, whisking occasionally. 

Add cooked pasta to sauce, and cook over medium, stirring constantly, until sauce thickens and coats pasta, about 3 minutes. Slice sausage at an angle into ½-inch-thick pieces; stir sausage, cubed squash, and red bell pepper into pasta mixture. Add salt and black pepper to taste; remove from heat. Divide pasta mixture evenly among 4 bowls, and top with black pepper, finely chopped parsley, and desired amount of grated Parmesan cheese. Serve immediately.