Cook the bacon. Cook the bacon in a large, deep skillet (or Dutch oven) over medium heat until crispy on both sides. Once it’s crispy, transfer the bacon to a paper towel-lined plate to drain off any excess fat. Let it cool and then crumble the bacon. (Don’t get rid of the bacon drippings in the pan, we’re using it in this recipe instead of oil or butter.)
Roast the butternut. Preheat the oven to 425F. Toss together the cubed squash, 3 tablespoons of bacon drippings, 3/4 teaspoon salt, and 1/4 teaspoon black pepper on a baking sheet, and then spread the squash out in a single layer. Roast the squash until tender and golden in places, about 20 to 35 minutes, tossing the squash once halfway through.
Cook the onion in the bacon drippings and then deglaze the pan. While the squash is roasting, add the sliced onion to the skillet that you cooked the bacon in with the remaining bacon drippings. Cook over medium heat until the onion is softened and starting to caramelize in spots, about 5 to 7 minutes, stirring occasionally. Add the garlic and cook 1 minute, stirring constantly. Add the wine, turn the heat up slightly, and cook until the wine is almost completely evaporated off, using a wooden spoon to scrape up any brown bits from the bottom of the skillet. Remove from the heat.
Puree the roasted butternut squash to make pasta sauce. To a blender, add 1 cup roasted butternut squash, half of the sautéed onion mixture, the chicken broth, heavy cream, remaining 3/4 teaspoon salt, remaining 1/4 teaspoon black pepper, and crushed red pepper flakes. Puree (carefully, it’s hot!) until the mixture is smooth and creamy. (See Notes.)
Combine. Pour the butternut squash pasta sauce into the skillet with the remaining half of the sautéed onions. Add the cooked and drained pasta, remaining roasted squash cubes, 3/4 cup shredded Parmesan, rosemary, thyme, and sage. Toss everything around gently to coat with the sauce.
Add the finishing touches and serve. Transfer to a serving platter and top with the crumbled bacon, remaining 1/4 cup Parmesan, and additional fresh rosemary, thyme, and sage leaves. Serve.
Notes
BLENDER SAFETY: When you're pureeing hot things, be careful not to overfill your blender. Additionally, make sure to vent the lid so the steam can escape. To do this, remove the cap on the lid and hold a kitchen towel over it while pureeing. Another option is to use an immersion blender.
Storage:You can store butternut squash sauce (before tossing with pasta) in an airtight container in the fridge for up to 5 days or in the freezer for up to 6 months. After tossing the sauce with the pasta, you can store it in the fridge for up to 4 days or in the freezer for up to 3 months.
Reheating: To reheat, thaw to room temperature and then reheat on the stovetop or in the microwave, adding a splash of water or broth as necessary.