Cut the top off of the butternut squash and cut in half lengthwise. Scoop out the seeds and inner membrane as much as possible. Place 3 garlic cloves in each cavity, drizzle with olive oil and flip over so the cut side is down on a baking sheet. Roast for 40-60 minutes or until tender when pressed. Remove and let cool until you are able to handle it.
Scoop out the flesh and place in a bowl. Peel the roasted garlic and toss in the same bowl.
Heat 1/4 cup of olive oil in a large stock pot. Add the onions, chopped sage and thyme and cook over medium high heat until the onions start to brown, about 10 minutes.
Add the squash, garlic and 2 quarts of stock. Bring to a bowl and then turn the heat down to medium low and let simmer for 20-25 minutes.
In a skillet, brown the sausage. Set aside.
In the same skillet, add a tablespoon more of olive oil (if the pan is dry) and fry the whole sage leaves turning to brown both sides. Remove to drain on a paper towel.
Salt the soup to taste and using an immersion blender, blend the soup until smooth. Add the sausage.
Ladle the soup into bowls and add 6 or 7 chunks of gouda cheese, fresh cracked pepper and a sprinkling of the crispy sage leaves.