Using a sharp knife, slice the butternut squash in half lengthwise. Be careful as the squash’s skin is quite tough! Using a spoon, scoop out the seeds and bit of flesh from the squash.
Spread 1 tablespoon olive oil over the squash halves. Place garlic cloves into each squash half. Add 1 tsp kosher salt and 1/2 tsp ground black pepper. Place sheet tray into the preheated oven and roast for 40-60 minutes, depending on the size of your butternut squash. You will know the squash is done when you can press it with a fork and it is soft.
While the squash is roasting, cook your pasta. Fill a large pot with water and bring to a boil. Add 2 tsp salt to your water. Add your pasta and cook 1 minute under the recommended time. You want your pasta to be “al dente” and have a little bite to it. Drain the pasta and set the pot aside to use again.
Let the squash cool for at least 10 minutes. After 10 minutes scoop the flesh of the butternut squash out and place into the bowl of a food processor. Be sure to scoop all the flesh and the garlic!
Add 1 cup of stock to the food processor. Process the mixture until it is smooth and creamy.
Place the pot you used for the pasta onto the stove and heat to low. Using a spatula spoon the butternut squash mixture into the pot. Add both the shredded gruyere and cheddar cheeses. Stir the cheeses into the butternut squash mixture until they are melted. At this point check your mixture for seasoning. Add additional salt and pepper to taste.
Add the cooked pasta to your squash and cheese mixture. Mix thoroughly.
Place pasta mixture into a 9×13 dish that has been coated with cooking spray.
Sprinkle 1/2 cup panko breadcrumbs over top of mac and cheese. Then top with herbs and drizzle 1 tbsp olive oil over top.
Bake for 25-30 minutes or until bubbly and golden brown on top. Allow to cool for 5 minutes, enjoy!