Goodness gracious, this stuffed squash is good. The crispy sausage combined with the roasted cranberries, cream sauce, and perfectly baked squash results in a flavor combination that honestly blew me away. In fact, my not-paleo father-in-law provided further validation after he asked me for the recipe when he got a taste on the day I took the photo of this recipe. So, if you’re looking to treat yourself or impress relatives, this one will not disappoint.

Check out nine other unique, paleo-friendly recipes here.


  • 1 pound hot Italian sausage removed from casings if using links
  • 1 acorn squash
  • 2 tsp. extra-virgin olive oil
  • ½ tsp. fine sea salt
  • 1/8 tsp ground black pepper
  • 1 cup fresh or frozen cranberries, coarsely chopped in a food processor
  • For the sauce:
  • ¼ cup mayo, store-bought or homemade
  • 2 tsp grated orange zest
  • 1 Tbsp fresh orange juice
  • 1 tsp chopped fresh rosemary


  1. In a frying pan over medium heat, crumble and brown the Italian sausage until it begins to get crispy. Remove the pan from the heat, and set aside.
  2. Preheat the oven to 350°. Using a sharp knife, cut the stem off the acorn squash and then turn it upside-down so that it sits on the cut side. From here, cut the squash into four wedges, and remove and discard the seeds. Rub the cut sides of each wedge with the olive oil, and place them skin-side-down in a small baking dish or pie pan. Sprinkle the tops of the squash with the salt and black pepper.
  3. Mix the cranberries into the cooked Italian sausage, and then spoon an equal amount of the mixture into the well of each acorn squash wedge. It’s OK if the sausage mixture spills over into the pan.
  4. Tent the dish with aluminum foil, and bake for 40 minutes, then remove the foil and return to the oven to bake uncovered for 20 more minutes, or until you can easily slide a fork into the flesh of one of the squash wedges.
  5. While the stuffed squash is baking, whisk the sauce ingredients together in a small bowl. Set aside.
  6. Let the squash cool for 5 to 10 minutes, then drizzle each piece with the rosemary orange cream sauce. Serve warm.
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