Heat the bacon in a pan over medium-high heat. Cook until the bacon is browned and crisp, but not burnt. Let the bacon cool on a paper towel and set aside.
Once the bacon has cooled, chop the bacon into bite-sized pieces. Discard the bacon fat but keep the pan nearby as you will use it for the sauce.
Heat the oven to 400 degrees. Line a baking sheet with parchment paper. Toss the butternut squash with one tablespoon of olive oil and spread evenly on the baking sheet.
Bake the squash for 25-30 minutes, stirring every 10minutes. (During the last 8-10 minutes of baking, you will add the kale and pepitas to roast).
While the squash is baking, cut or rip 1-inch pieces of kale and place them into a bowl. About 10 minutes before the squash is about to come out of the oven, toss the kale and pepitas with ½ tablespoon of olive oil.
Remove the baking sheet from the oven and stir the squash one last time. Add the kale and pepitas on top, spreading lightly and evenly. Roast for8-10 minutes or until kale is slightly crispy and butternut squash is nicely browned.
Cook the pasta according to the package directions. Drain and aside in a large bowl.
Heat the original pan over medium heat and add the remaining 3tablespoons of olive oil. Add the minced garlic and cook for about one minute or until fragrant.
Add the salt, pepper, red pepper flakes, and wine. Stir well for 2-3minutes.
Add the butter and let it melt. Stir to combine all ingredients.
In a large bowl, combine the pasta, butternut squash, kale, pepitas, and chopped bacon. Pour the sauce over the pasta and toss lightly.
Serve warm with freshly chopped parsley and freshly grated parmesan or romano cheese as garnish.