Preheat oven to 425°F. Line a large sheet pan with parchment paper.
Add butternut squash to the prepared pan and drizzle with 2 tablespoons olive oil; season with 1 teaspoon salt and 1/4 teaspoon black pepper. Roast for 25-30 minutes until the squash is fork-tender. Remove from oven and slightly cool.
Cook pasta according to packaging instructions. Drain and reserve ½ cup of starchy water.
In a small skillet, heat remaining ¼ cup of oil over medium-high heat until hot. Fry sage leaves until crisp, 2–3 seconds. Transfer with a fork to paper towels and sprinkle with salt. Set aside.
In the same skillet used to fry the sage, discard all but 2 tablespoons of oil. Over medium-high heat, sauté the shallots until fragrant and tender, about 3-4 minutes. Add the garlic, and sauté for 20-30 seconds.
Transfer squash, chicken broth, shallots, garlic, and remaining salt and black pepper to a blender. Puree mixture until smooth. Add cream and continue to blend for 20-30 seconds. Slowly pour in reserved starchy water and nutmeg.
Combine the butternut squash cream with the cooked pasta. Season with salt and pepper, if needed. Top with parmesan cheese and crispy fried sage if using. Enjoy!
