This hearty autumnal baked pasta is perfect for game day, make-ahead weeknight dinners and entertaining all season long. Luscious homemade butternut squash alfredo sauce coats a combination of soft cheese tortellini, tender chicken and kale — plus sundried tomatoes for brightness and acidity. We top it all off with Havarti and Parmesan, then bake until bubbling and gooey.
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Directions
Preheat the oven to 450 degrees F.
Toss the squash, garlic, shallots, 2 tablespoons of the olive oil, 1 1/2 teaspoons of the dried oregano, 3/4 teaspoon salt and several grinds of black pepper in a large bowl until evenly combined. Transfer to a rimmed baking sheet and spread into an even layer. Bake until the squash is tender and golden brown in spots, about 25 minutes.
Meanwhile, bring a large heavy-bottomed pot of generously salted water to a boil over medium-high heat. Add the tortellini and cook for 3 minutes. Add the kale and cook until bright green and tender and the pasta is al dente, about 1 minute more. Reserve 3/4 cup of the pasta water, then drain the pasta and kale and transfer to a large bowl; set aside. Return the pot to the stove.
Transfer the roasted shallots and garlic to a blender along with half of the squash. Add the remaining squash to the bowl with the pasta and kale. Add the heavy cream, 1/2 cup of the Parmesan, 1/4 teaspoon salt, several grinds of black pepper and the reserved pasta water to the blender and blend until very smooth, 1 to 2 minutes; set aside.
Add the remaining 1 tablespoon olive oil to the reserved pot and place over medium-high heat. Sprinkle the chicken with the poultry seasoning, crushed red pepper flakes, remaining 1 1/2 teaspoons dried oregano and 1/4 teaspoon salt. Add the chicken to the pot and cook, stirring occasionally, until just cooked through and golden brown, 4 to 5 minutes. Reduce the heat to medium low. Stir in the sun-dried tomatoes and butternut squash sauce. Stir in the pasta, kale and reserve roasted squash until evenly combined. Taste and adjust the seasoning with salt and black pepper.
Transfer to a 9-by-13-inch baking dish. Sprinkle evenly with the Havarti and remaining 1/4 cup Parmesan. Bake until the cheese is melted and bubbling at the edges, about 15 minutes. Let rest for 5 minutes, then serve.
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