Roasted Winter Squash Soup with Gruyère Croutons

I'm not sure when or why it started, but for the last few years it's been a tradition in my family to have Roasted Winter Squash Soup for dinner on Christmas Eve. We've always opened our presents from one another on Christmas Eve (the ones from Santa are there for us on Christmas morning after he comes down the chimney and stuff...) and cook a big feast on Christmas day, so I suspect this started as a delicious, comforting, wintery meal we could have by the fire as we got ready to sit down and open presents.

This recipe is based largely on one I found at Epicurious, with the major difference being that we roast the squash rather than boiling it. There are two reasons for this. First and foremost is that roasted squash tastes approximately one million times better than broiled squash. The secondary (but also important) reason is that I have never met anyone with the time or patience to sit down and peel raw acorn squash. (I saw Martha Stewart pretend she was going to on her show once, but she immediately set it down and switched over to a squash that her minions had peeled for her...)

The seeds from the squash are great roasted up in a little butter and garlic salt as well, so it's worth the effort to wash them off and roast 'em up.

Roasted Winter Squash Soup with Gruyere Croutons
   For the Soup
      3 - 5 pounds butternut squash
      3 pounds acorn squash
      olive oil
      1 teaspoon + 2 - 3 teaspoons minced fresh thyme
      1 teaspoon + 2 - 3 teaspoons minced fresh sage
      1/4 cup butter
      1 large onion, finely chopped
      12 – 36 large garlic cloves, peeled
      6 cups chicken stock
      1/4 - 1/2 cup heavy cream

   For the Croutons
      24 1/4-inch-thick baguette bread slices
      1 C grated Gruyère cheese (plus additional to serve)
      1 t minced fresh thyme
      1 t minced fresh sage

For the Soup: Halve the squash and sprinkle with olive oil and 1 teaspoon each of minced sage and thyme. Place 4-8 cloves of peeled garlic in each cavity and roast at 375°F until tender (about 1 - 2 hours). Roast additional garlic wrapped in foil if desired. When cool enough to handle, scoop the roasted squash and garlic out of its skin and set aside.
Melt the butter in a large pot over medium heat. Add the onion sauté until tender, about 10 minutes. Add the additional 2 - 3 teaspons each of sage and thyme and cook until very fragrant, about 1 minute. Add the broth along with the roasted squash and garlic and bring to boil. Reduce heat, cover and simmer about 20 minutes. Working in batches, purée the soup in a blender. Return the soup to the same pot and stir in cream. Bring to simmer and season to taste with salt and pepper. (Can be made 1 day ahead. Chill. Rewarm over medium heat before serving.)

For the Croutons: Preheat the broiler. Arrange the bread on a baking sheet and broil until golden, about 1 minute. Turn the bread slices over and sprinkle the other side with the cheese and remaining herbs. Broil until cheese melts, about 1 minute.

Ladle soup into bowls. Top each with croutons and serve. Serve additional grated Gruyère if desired.

Serves 8-10.