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Preheat the oven to 425 degrees Fahrenheit.
Peel the outer layers of the whole head of garlic, making sure to leave the garlic cloves intact.
In a 13×9 baking dish, add the cherry tomatoes, shallot, oregano, thyme, basil, and crushed red pepper. Place the head of garlic in the center of the baking dish.
Drizzle with olive oil, and season with salt and pepper to taste.
Bake for 40-45 minutes or until tomatoes burst and garlic is nice and tender.
In the meantime, cook the pasta according to the package instructions until al-dente. Reserve 1 cup pasta water
Remove the tomato mixture from the oven and let cool slightly. Transfer to a high-speed blender with the heavy cream. Blend until smooth.
Transfer to a pot with the cooked pasta, Parmesan cheese, and pasta water, if needed. Stir to combine.
Serve warm.