Preheat your oven to 425 degrees. Place the chopped butternut squash onto a lined baking sheet, drizzle with 2 tbsp of olive oil and season with 1/2 tsp salt. Toss to get everything evenly coated and roast for 30-35 minutes, until the squash is golden brown.
While the squash is in the oven, cook the pasta. Fill a large pot with water and cook according to package instructions. Once cooked, drain the pasta and put it in a large serving bowl.
When the squash is done roasting, transfer it to the same serving bowl as the pasta. Then add in the kale, pecans, cranberries, sage, and goat cheese. Gently toss to combine.
To make the vinaigrette, add the red wine vinegar, olive oil, salt, and pepper to a jar with a tight fitting lid. Give it a good shake to combine. Then pour the vinaigrette over the pasta dish. Gently toss to make sure everything is coated in the vinaigrette.
Serve and enjoy!