Hearty Stuffed Autumn Squash

The classic combination of sweet and spicy makes this recipe irresistible. Spicy olive oil & Italian sausage pair with sweet balsamic vinegar & squash for a filling meal or a hearty side dish.

This recipe serves 2 as a main course or 4 as a smaller meal with other sides (we love to serve it with an arugula salad or steamed green beans!). 


  • 3 tablespoons spicy olive oil from The Olive Scene, divided (such as Chipotle, Harissa, Cayenne, or Baklouti Oil)

  • 3 tablespoons Black Currant Balsamic Vinegar, divided

  • 1 medium or large acorn squash

  • ½ teaspoon kosher salt

  • ¼ teaspoon freshly ground black pepper

  • 6 oz spicy Italian sausage, bulk or with casings removed (pork, turkey, or chicken sausage all work well)

  • 1 small leek, sliced (white and light green parts only, rinsed thoroughly)

  • 1 clove garlic, minced

  • 2 cups tightly packed baby kale or torn kale leaves

  • 3 tablespoons reduced-sodium chicken stock

  • ¼ cup pine nuts or pepitas

  • 2 tablespoons grated fresh Parmesan

  • 2 tablespoons panko breadcrumbs

  • 1/2 tablespoon of your favorite roasted nut oil from The Olive Scene (Pecan, Walnut or Pumpkin Seed Oil)


  1. Preheat oven to 375°.

  2. Optional step to make cutting the squash easier: using a fork, poke each squash 5-6 times so steam can escape. Put in microwave on high for 2 minutes. Remove carefully and let cool a couple of minutes.

  3. Halve the squash down the middle, and remove the seeds. Cut a thin slice off the round bottom side of each squash half to create a stable base for when filling and broiling the squash. Score the inside of the squash with a sharp knife and brush each half with 1/2 tablespoon of oil and 1/2 tablespoon of vinegar. Allow to sit upright for 5 minutes for the oil and vinegar to penetrate the scoring. Sprinkle squash with salt and pepper.

  4. Coat a foil-lined baking sheet with cooking spray, place squash flesh side down and bake until golden and tender, 30 - 40 minutes. Remove from oven; flip squash and set aside.

  5. While the squash is cooking: Heat 1 tablespoon olive oil in a large nonstick skillet over medium heat. Cook the sausage through, breaking into pieces (about 6 minutes), and transfer to a paper towel-lined dish to drain.

  6. Add final tablespoon of olive oil to the same pan and cook the leeks until soft, about 3 minutes. Add the garlic and cook until fragrant, about 30 seconds. Add kale and combine. Add the chicken stock and 1 tablespoon balsamic vinegar. Cook until kale is tender, about 5 minutes, Stir in sausage and remove from heat.

  7. When the filling is cooked and the squash is done roasting, divide the filling between the squash “bowls.”

  8. Combine the nuts, Parmesan, panko breadcrumbs, and nut oil in a small bowl. Sprinkle evenly over squash. Broil under a low broiler until the topping is golden brown, about 2 minutes.

  9. Let cool 5 minutes and drizzle remaining Black Currant Balsamic Vinegar over the finished squash before serving. If serving 4, cut each half into half again at the table.

Recipe adapted from Epicurious