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Sausage and Apple Stuffed Acorn Squash (The Cut-Side-Down Trick)

Sausage and apple stuffed acorn squash roasted cut-side down for real caramelization, then filled with a cider-deglazed sausage stuffing enriched with the squash’s own flesh.

  • Total Time: 1 hour 10 minutes
  • Yield: 4 1x

Ingredients

Scale
  • 2 medium acorn squash, halved and seeded
  • 3 tbsp olive oil, divided
  • 1 lb sweet or spicy Italian sausage, casings removed
  • 1/2 cup diced yellow onion
  • 2 cloves garlic, minced
  • 1 medium apple (Honeycrisp or Gala), diced small
  • 1/4 cup hard apple cider (or apple cider + 1 tsp cider vinegar)
  • 2 tbsp fresh sage, chopped (or 1 tsp dried)
  • 1/2 cup shredded gruyere or sharp white cheddar
  • 1/4 cup toasted pepitas or chopped walnuts
  • Salt and black pepper, to taste

Instructions

  1. Preheat oven to 400°F (200°C). Brush the cut sides of the squash halves with 2 tbsp olive oil and season with salt and pepper.
  2. Place the halves cut-side down on a parchment-lined sheet pan and roast for 25 minutes, until a fork pierces the skin easily and the cut edges are golden.
  3. Flip the squash cut-side up and let cool slightly. Scoop out a thin layer of flesh from each cavity, leaving a sturdy shell, and set the scooped squash aside.
  4. While the squash roasts, heat remaining oil in a skillet over medium-high. Add the sausage and cook, breaking it up, until browned, about 6 minutes.
  5. Add the onion and garlic to the skillet and cook until softened, 3 minutes. Pour in the hard apple cider to deglaze, scraping up any browned bits, and let it reduce for 1 minute.
  6. Stir in the diced apple, sage, and reserved squash flesh. Cook 2-3 minutes, until the apple softens but still has bite. Season to taste.
  7. Divide the filling among the squash shells, mounding it generously. Top with shredded cheese.
  8. Return to the oven and bake at 400°F for 12-15 minutes, until the cheese is melted and lightly browned.
  9. Scatter with toasted pepitas or walnuts before serving.

Notes

Roasting cut-side down is the whole trick — don’t skip it or skip the flip, or the squash will steam instead of caramelize. Make the filling a day ahead and stuff cold squash shells before the final bake if you’re prepping for a crowd. Leftover filling freezes well on its own for up to 2 months, even without the squash.

  • Author: Ella Whitley
  • Prep Time: 15 minutes
  • Cook Time: 55 minutes
  • Method: Roasted
  • Cuisine: American