Creamy Winter Squash Soup and Fancy Grilled Cheese Sandwiches

20091005-Winter Squash Soup and Grilled Cheese

A few weeks ago we received this strange, bul­bous, warty squash from our CSA. We had no idea what it was. After some research we dis­cov­ered that it was a Hubbard squash. I read that their flesh tends to be very moist and they they need to be cooked longer but that they are per­fect for roast­ing. Over this last week­end we decided that it would be a great soup and I got to work break­ing it down (the squash, that is). Due to its large size — twelve inch diam­e­ter at least — it was very dif­fi­cult to split, but once I got it open, the rest was easy. Once roasted, its meat was soft and a won­der­ful burnt orange color and some­what rem­i­nis­cent of pump­kin in both tex­ture and taste. Keep read­ing for the recipe and more pictures.


Full of fall fla­vor, this hearty soup was per­fect for din­ner last night as I’ve been fight­ing off a cold which is try­ing its darnedest to get the bet­ter of me. For me, there is no bet­ter com­pan­ion to soup, espe­cially when feel­ing under the weather, then a warm sand­wich. I wanted grilled cheese, but done up a lit­tle more fancy than usual. Instead of the stan­dard ched­dar we used extra sharp white ched­dar and brie and added sliced pear and used whole wheat sour­dough for the bread. It was the per­fect fall meal.

Even though I used a Hubbard squash, any sort of win­ter squash like pump­kin or but­ter­nut would work well. To roast the Hubbard, I sliced it in half, removed the seeds and placed it cut-side down on rimmed bak­ing sheets, roast­ing for 50 – 60 min­utes in a pre­heated 425ºF oven. Then just scoop out the flesh and dis­card the skin.


While the squash is roast­ing you can throw a red pep­per in with it to roast for 30 min­utes, peel­ing its skin after. Also, I used bacon as a starter for this recipe because we had some that needed to be used. You can eas­ily skip it and use a cou­ple table­spoons of olive oil for the sautéing instead, cre­at­ing a lower fat and won­der­ful veg­e­tar­ian soup.

Creamy Winter Squash Soup

4 Strips of Bacon
1 Yellow Onion, Diced
1 Clove Garlic, Minced
1 cup sliced Shitake Mushrooms, Stems Removed
2 Whole Cayenne Peppers, Seeded and Diced
1 Whole Red Bell Pepper, Roasted, Seeded and Diced
8 Cups Roasted Winter Squash
1 cup Milk
1 1/2 cup Unfiltered Apple Juice
1 cup Cranberry Juice
1/2 cup Grated Parmesan
1/2 tsp. Nutmeg
1/4 tsp. Allspice
1/8 tsp. Cloves
1/4 tsp. Cayenne Powder
1 tbsp. Chopped Fresh Basil
1 tsp. Chopped Fresh Sage
1 tsp. Chopped Fresh Flat Leaf Parsley
1/2 tsp. Chopped Fresh Thyme

Preheat an eight quart stock pot over medium-high heat. Slice bacon into quarter-inch strips and put in the pot. Fry bacon until crispy and remove with a slot­ted spoon to paper towel to drain.

Sauté onion in the remain­ing bacon grease for a cou­ple min­utes and then add the gar­lic, mush­rooms, cayenne and roasted red pep­per. Continue cook­ing for 8 – 10 min­utes until the onion is translucent.

Place half the roasted squash in a blender with the milk and pureé until smooth and pour into the pot. Repeat with remain­ing squash and apple juice. Once all the squash mix­ture is in the pot, add cran­berry juice, Parmesan and remain­ing herbs and spices, stir­ring well to com­bine all ingre­di­ents. Simmer for at least half an hour before serving.

Serves 6 – 8


I gar­nished the soup with a lit­tle reserved bacon and sliced mush­rooms. It was really nice to stir in just before eating.


Look at that gooey, melty cheese…YUM!


Long live the soup and sandwich!

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  1. Posted October 6, 2009 at 4:16 pm | Permalink

    diz­zam that a sexy cheese melt!

    totally mak­ing this soup. thanks! :)

  2. Posted October 6, 2009 at 5:44 pm | Permalink

    hey ben, this ingre­di­ent list may be a tetch long – but I wouldn’t elim­i­nate a thing. Bacon and shi­itakes – nice touches! This would work beau­ti­fully with any win­ter squashes. Soup time is here.

  3. Posted October 6, 2009 at 6:17 pm | Permalink

    nancy, haha, yeah, my wife teased me about hav­ing to shut off the water to the house so i can put the kitchen sink in the soup, but in the end, it was worth it.

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