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Preheat oven to 400 degrees. Cut the squash in half, and lay them flesh side up. Scoop out the seeds — I like to use an ice cream scooper. Sprinkle 1 tsp of the oil over the squash flesh. Place the squash flesh side down on a baking sheet and place in the oven.
Cut the root end off the head of garlic, exposing the bottom of the garlic cloves. Drizzle exposed cloves with 1 tsp of the olive oil. Wrap the garlic in aluminum foil, place on the baking sheet next to the squash in the oven.
The squash and the garlic will both take about 40 minutes to roast. After 40 minutes, remove the baking sheet to check for doneness. The squash is done when the skin pierces easily with a fork. If it does, turn the squash over — when roasted the flesh should be soft and beginning to brown. The garlic is done when the cloves have become quite soft and beginning to brown. If they are done, remove the squash and garlic and set aside to cool; or return to roast for another 5 minutes or so as needed.
Start boiling a large pot of water for cooking the pasta with about 10 minutes roasting time left. Add the pasta after you’ve started cooking the sauce on the stovetop.
Place the white wine and 1 tablespoon olive oil in a large skillet or medium sauce pan (see notes). Squeeze the roasted garlic out of the skin and into the sauce pan. Heat the garlic on medium, then add the roasted squash flesh, and the tofu if you are using it. Stir to combine, and cook on medium low. Stir every few minutes.
Add the pasta to the boiling water after adding the squash to the sauce pan. Cook according to package directions as you finish the sauce.
Add the milk to the sauce, stir to combine. After the pasta has been cooking for at least 5 minutes, scoop out 1/2 cup of pasta cooking water. Pour some of the pasta water into the sauce, stir to combine. Add up to 1/2 cup of the cooking water to the sauce to achieve desired consistency. This is a fairly thick sauce but you want it to have enough liquid to combine well with the pasta. Keep the sauce warm as the pasta finishes cooking.
When the pasta is cooked, drain, and toss immediately with the acorn squash sauce. Add the cheese, salt and pepper to taste, and parsley. Plate the pasta, and pass additional cheese at the table. Enjoy!