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Squash Soup with Leeks and Peppers

I wanted to transform a favorite pizza topping into a soup.  I bought a very large pumpkin, beige and very intensely orange inside, but it was not as sweet and richly flavored as I'd hoped.  A little hit of popcorn sauce corrected that perfectly, but next time I'll try to find some more reliably sweet squash, like butternut, sweet dumpling, or small pie pumpkins.   It sounds like an enormous amount of squash, but this is not diluted with stock or water; the pureed squash is the entire body of the soup. 

8-10 pounds of winter squash 

1-2 tablespoons olive oil

1-2 tablespoons butter
About 2 cups of leeks, sliced (I like to slice them lengthwise to spread and clean between the layers, then slice crosswise into 1/4 inch or less pieces)
4-5 large ripe red bell peppers, or 2 lbs of another sweet, ripe, red pepper, hotness to your preference

2-3 tablespoons of ground or rubbed sage

4 ounces of strong hard grating cheese (I love dry jack, but this would be excellent with parmesan or pecorino toscano as well)

Salt and freshly ground pepper

Honey and/or molasses (optional)

Halve, seed, and bake the squash at about 350-400 degrees, cut halves down on baking sheets, until soft.  For the very large pumpkin I used, this was more than an hour; for thinner dumpling squash, it could be 30 minutes.  Alternatively, microwave squash, cut side down, until very soft.  

Scrape out the cooked squash flesh into a large pot or bowl.   This several quart mass of squash needs to be pureed--I used a stick blender right in the bowl, but a food processor or food mill would also work.  If using a regular blender, it may be very difficult without adding extra water.  

In a 5-8 quart soup pot, saute the leeks and peppers in the butter and oil for a few minutes, until they're translucent.  Add the squash, and warm over low heat while you add the grated cheese, stirring constantly to prevent the cheese from clumping and prevent burning.

Season to taste with sage, salt, pepper, and, if the squash was not sweet enough, pour in a little honey and/or molasses.

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