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Heat the oven to 350°.
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Halve the acorn squash, and place 1/2 tsp butter and brown sugar in the hollow of each half, and a dash of cinnamon.
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Bake in the oven for 30-45 minutes, or until the flesh is easily speared with a fork.
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In a large pot on the stove, melt the remaining tsp of butter, and add the apple pieces. Cook them on medium temperature, until they are soft and easily speared with a fork, about 10 minutes.
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Add the broth to the soft apples.
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With a spoon, carefully scoop out the acorn squash into the pot. It's hot! Use an oven mitt to hold the squash if you have to. (It will look gross. Heads up.)
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Blend with either an immersion blender, or a stand blender with the plastic piece of the blender removed, and holding a cloth over the hole (if you leave the plastic centre in, pressure will build because of the hot soup and you'll end up with soup all over your kitchen!)
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Stir in the heavy cream, and add nutmeg and cloves.