Preheat oven to 375°F. Line a baking sheet with parchment paper.

Slice ¼ inch off the top of a head of garlic, exposing the tops of the cloves inside. Drizzle cut garlic with 1 tablespoon evoo, and wrap in foil. Roast in a 375°F oven for 40 to 50 minutes, or until the cloves are soft and lightly browned.

Meanwhile, cut squash between the neck and the bell. With a sharp knife, score around the neck, then firmly cut down on the scored line. Peel the neck with a sharp knife or vegetable peeler. Reserve the bell of the squash for another recipe.

Lay squash on a cutting board with a wooden spoon on either side. Make cuts ¼ inch apart, and as far down as the wooden spoons will allow.

Generously rub squash with 2 tablespoons of evoo, and season with salt and pepper. Roast squash on prepared sheet at 375°F for 30 minutes.

Squeeze garlic out of head and smash with a fork. Mix garlic puree with bread crumbs, rosemary, thyme, crushed red pepper and cheese, if using. Add 2 tablespoons of evoo to form a thick paste. Season with salt and pepper.

Rub squash with 1 tablespoon more of evoo, and rub paste on squash, getting the bread crumb paste into the cuts. Return squash to oven and roast for 20 to 30 minutes more, or until browned and crispy on top.

Cut squash into portions and serve as a side dish, or vegetable main.