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A closeup image of sausage stuffed squash on a plate.

Cheesy Sausage Stuffed Delicata Squash Recipe (video)

40 minutes prep + 45 minutes cook
8 servings
Creamy, cheesy sausage stuffed delicata squash with orzo pasta, smoked cheese, pecans, and dried cranberries! Great for fall dinners and Thanksgiving!

Ingredients 
US Customary - Metric

  • 4 medium Delicata squashes, or 5 smaller ones
  • 1 tbsp avocado oil
  • 1 lb mild Italian sausage
  • 1 large shallot, finely diced
  • 4 medium garlic cloves, finely minced
  • 1 tsp sea salt
  • ground black pepper, to taste
  • 1 tbsp fresh thyme
  • 2 tbsp chopped fresh parsley
  • 2 tbsp port, or sherry wine
  • 1/2 cup orzo pasta
  • 1/4 cup dried cranberries, chopped; divided
  • 1/4 cup diced pecans, divided
  • 1 cup chicken broth
  • 1/2 cup whole milk, or half-and-half
  • 6 oz smoked white cheddar, grated (I use Beecher's Smoked Cheese)
  • 1/4 cup chopped fresh parsley, for garnish
  • 1/4 cup pomegranate arils, for garnish; optional

Instructions

Preparing the Squash:

  • Preheat the oven to 400°F. Line a large baking sheet with parchment paper.
  • Wash and dry the squash first, then use a sharp knife to carefully cut off the hard ends/stems on each squash.
  • Carefully split each squash down the middle, lengthwise. Use a spoon to scoop out the seeds and discard them.
  • Place the squash with the open side down onto the lined baking sheet.
  • Roast the squash uncovered at 400°F for 25 minutes, just until the squash is tender.

Making the Filling:

  • For the filling, preheat a large sauté pan over medium heat and add a drizzle of avocado oil.
  • Add the Italian sausage and use a wooden spoon to break apart the ground meat into small pieces. Cook the sausage for 5 to 7 minutes, until it’s nicely browned.
  • Next, add the diced shallot and minced garlic. Stir and cook for about 2 minutes, until softened.
  • Season the mixture with salt, pepper, thyme, and parsley. Pour in the port or sherry and deglaze the pan, scraping off the browned bits from the bottom of the pan.
  • Stir in the orzo pasta, 2 tablespoons of chopped dried cranberries, and 2 tablespoons of diced pecans.
  • Pour in the chicken broth and milk, then cover the pan with a lid. Cook the filling over medium-low heat for 7 to 10 minutes, stirring every few minutes, until the orzo pasta is cooked and most of the liquids have evaporated.
  • Remove the mixture from the heat and stir in the grated cheese.

How to Make Stuffed Squash:

  • Use tongs to carefully turn the roasted squash over for filling.
  • Fill each squash half generously with the sausage filling, creating a little mound over the top.
  • Garnish the top of the stuffed squash with more chopped fresh parsley and the remaining dried cranberries and diced pecans.
  • Return the stuffed squash back into the oven and bake at 400°F for 20 minutes, uncovered.
  • Once baked, garnish the stuffed squash with more parsley and pomegranate arils, if desired, and enjoy!

Nutrition

Serving: 1half | Calories: 473kcal | Carbohydrates: 35g | Protein: 18g | Fat: 30g | Saturated Fat: 11g | Polyunsaturated Fat: 4g | Monounsaturated Fat: 13g | Cholesterol: 67mg | Sodium: 972mg | Potassium: 1071mg | Fiber: 5g | Sugar: 10g | Vitamin A: 3621IU | Vitamin C: 36mg | Calcium: 261mg | Iron: 3mg