Winter squash isn't a typical ingredient in this classic Italian American pasta dish, but the spicy, creamy pink sauce is the perfect foil for its sweet flavor. If you're a stickler for seasonal herbs, swap out the basil for chopped arugula (especially the peppery mature variety).
3-4 pounds winter squash, such as butternut or kabocha (peeled if using butternut), seeded, and cut into 3/4-inch pieces (about 4-1/2 cups)
4 tablespoons olive oil, divided
1 teaspoon granulated sugar
3 teaspoons kosher or sea salt, divided, plus 1 tablespoon for pasta water
Freshly ground black pepper
1 small red onion, diced
3 medium-size garlic cloves, minced
1/4-3/4 teaspoon crushed red-pepper flakes (see "Note," below left)
1 (28-ounce) can whole tomatoes, coarsely chopped, juices reserved
1/2 cup vodka
2/3 cup heavy cream
1 pound dried pasta (see "Note," below left)
1 cup finely grated Parmigiano-Reggiano cheese, plus extra for garnish
1/3 cup chopped fresh basil
Heat oven to 450°. Toss squash with 2 tablespoons olive oil, sugar, 2 teaspoons salt, and a generous grind of pepper. Roast until tender and browned on the edges, 25-30 minutes, stirring once partway through cooking. Meanwhile, bring a large pot of water to a boil over high heat. Add 1 tablespoon salt to the water for cooking.
While squash is roasting, heat the remaining 2 tablespoons olive oil in a large saute pan or skillet over medium heat. Add onion and cook, stirring occasionally, until softened and starting to brown, about 6 minutes. Add garlic and red pepper, stirring to combine, and cook until garlic is fragrant, about 1 minute. Stir in tomatoes (with juices), vodka, and 1 teapoon salt; cook an additional 10 minutes, stirring occasionally, lowering heat if sauce starts bubbling too vigorously. (You want a gentle simmer.) Stir in cream, cook an additional minute, and set aside.
While sauce is simmering, turn water to high heat and cook pasta according to package directions, until just al dente. Reserve 1/4 cup cooking water and set aside.
Drain pasta, return it to the pot over medium-high heat, and toss with squash and reserved pasta water. Stir in tomato-vodka sauce and cheese until thoroughly combined. Cook until sauce is thickened and pasta is nicely coated, about 3 minutes. Remove from heat, toss with basil, sprinkle with extra cheese, and serve.
Note: The sauce gets its fiery kick from red-pepper flakes; those with sensitive palates may want to use less of that ingredient. Any short dried pasta will work here; we're particularly fond of farfalle ("bow ties") and traditional penne rigate.