Cut the ends off of the squash to provide a flat, stable surface. Stand the squash on one end and use a vegetable peeler to remove the skin. Slice a few rounds off of the small end to shorten the squash, and then cut down through the center of the thick end to expose the center. Use a spoon to scoop out the seeds and center pulp. Cut the remaining squash into small cubes.
Heat 2 Tbsp of olive oil in a large pot or skillet over medium heat. Once the oil is hot, add the cubed squash, sage, salt & pepper (a generous sprinkle). Saute until the squash tender (about 10-15 min). They will looks slightly translucent and will start to smash a little like a cooked potato. Taste a cube or two to make sure they’re cooked through. Turn the heat off.
While the squash is cooking, cook the pasta. Bring a pot of water to a boil and add a generous sprinkle of salt to the pasta water for flavor. Cook the pasta according to the package directions (boil for 7-10 minutes or until al dente). Drain the pasta.
Once the squash is tender and the pasta is drained, add the pasta, cranberries, and chopped parsley to the pot. Stir to combine.
Drizzle the last 2 Tbsp of olive oil over everything and add salt and pepper to taste. Lastly, stir in the shredded parmesan. Serve warm!