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Preheat oven to 400 degrees.
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Place squash with cut side up in greased baking pan.
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Place one teaspoon butter plus one teaspoon brown sugar in each acorn half.
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Cover squash with aluminum foil and bake until tender, approximately 30 minutes.
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Scoop cooked squash out of shells, leaving 1/4 inch thick shell.
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Mix cooked squash, pineapple, 1 tablespoon butter, and nutmeg. Beat until smooth.
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Spoon mixture into shells; heat at 425 degrees for approximately 15 minutes.