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Preheat oven to 400 degrees.
Drizzle squash and garlic with olive oil and sprinkle with salt and pepper. Wrap the garlic in foil, and add the garlic and squash to a parchment lined baking sheet. Roast for 45 minutes. Let cool a bit until easier to handle.
To a food processor or blender, scoop out the squash flesh and squeeze in the garlic. Add the goat cheese, honey, and a sprinkle of salt and pepper. Blend until nice and smooth.
Add bacon to a large saute pan or Dutch oven. Turn on heat to medium. Let cook, continuously stirring. Once nice and crispy, add the rosemary and red pepper flakes. Stir and let cook for 30 seconds-1 minute. Turn heat off until the pasta is ready.
Cook the Orecchiette in salted water 30 seconds short of al dente. Add the pasta directly to the pot with the bacon. Scrape up the brown bits on the bottom of the pan (the excess pasta water should loosen the fond). Add the squash/goat cheese mixture and a ladle full of pasta water. Mix and add more pasta water until the sauce is silky, not thick, and coats the pasta. I added another ladle full of water. It's ready when the pasta is perfectly al dente.
To serve, add a grating of Parmesan cheese and sprinkle of black pepper.