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1
For the squash: Preheat the oven to 400 degrees F.
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2
Place the squash on a baking sheet flesh-side up and rub with the olive oil.
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3
Season liberally with salt and pepper.
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4
Roast until the edges begin to ripple and a poke with a fork reveals tender flesh, about 40 minutes.
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5
Allow to cool until easy to handle.
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6
Lower the oven temperature to 350 degrees F.
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7
Use a spoon to scoop out the flesh into a large bowl, leaving about 1/4 inch of flesh within the skin of each squash half to help it maintain its shape.
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8
For the filling: In a large pan on medium-high heat, add the olive oil and sausage.
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9
While cooking, break the sausage into bits like ground meat with a wooden spoon.
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10
Once some of the fat is rendered from the sausage, add the onions, paprika, pumpkin pie spice, sage, celery, bell peppers and a pinch of salt.
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11
Cook until the sausage is done and the vegetables are tender.
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12
Add the mixture to the bowl of squash along with the cheese, walnuts and cranberries and stir to combine.
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13
Taste and season with salt and pepper if needed.
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14
Fill the hollowed squash halves with the mixture and place back in the oven to melt the cheese and make the tops golden brown, 15 more minutes.
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15
Sprinkle with parsley and serve warm.
