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A velvety, slightly sweet soup made from roasted butternut and acorn squash, topped with crispy bacon.
Preheat oven to 375 F. To prep the squash, cut about an inch off the bottom and top of each squash so you have both a flat surface to place on a cutting board and underneath the surface of a knife as you cut. Use a heavy chef’s knife to halve each squash and place the halves cut-side down in a 9×13 Pyrex baking dish. I needed two dishes to hold my 8 squash halves. Fill each dish with about 1/2 an inch of water and bake in the oven at 375 F for about 60-80 minutes, or until a fork pierces the flesh of the squash easily.
Remove squash from the oven and let it cool on the counter. Once they are cool enough to handle, take a spoon and scoop out all the seeds. Then scoop the cooked flesh away from the skin and put it into a bowl. Discard skin and mash the roasted squash with a potato masher. Now you are ready to prepare your soup.
Heat butter in stock pot over medium heat. Add onions and reduce heat to medium low. Cook, stirring occasionally, until onions are deeply caramelized, about 30-40 minutes.
Then turn heat to medium high. Add wine and scrape up any browned bits from bottom of pot. Bring to a boil and add chicken broth, roasted squash, and seasonings (maple syrup through black pepper). Stir the soup well and bring to a simmer.
Remove soup from heat and add the cream cheese. Using an immersion blender, blend the soup until very smooth. Taste, adjust seasonings, and put back on medium heat until just simmering.
Serve soup topped with crispy bacon crumbles.
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