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Stuffed Winter Squash

Hearty winter squash stuffed with spicy sausage, apples, kale, and aged cheddar. A cozy recipe on repeat for the cold days ahead.
Prep Time15 mins
Cook Time1 hr
Total Time1 hr 15 mins
Course: Main Course
Cuisine: American
Keyword: fall, healthy


  • 6 small or 3 medium winter squash
  • 2 T olive oil divided
  • S&P
  • 2 shallots chopped
  • 1.5 lbs spicy pork sausage
  • 1-2 apples diced
  • 4 cups kale washed and torn into bite-size pieces
  • 2 tablespoons heavy whipping cream
  • 1.5 cups aged cheddar cheese


  • Preheat oven to 400 F. If using small squash, cut the tops off. If using medium squash, cut in half. Scoop out seeds. Brush with 1 tablespoon olive oil and season with salt and pepper. Place on baking sheet and roast for 20-45 minutes depending on size (20-30 for small; 35-45 for medium). Remove once tender and set aside until stuffing is ready.
  • Meanwhile, heat remaining 1 tablespoon olive oil in large nonstick skillet over medium heat. Add shallots and saute 2-3 minutes. Add sausage, breaking up with a wooden spoon, and cook until just browned (if there is a significant amount of fat in the pan, you could drain at this time). Add apples and kale, stirring until kale has significantly cooked down. Add cream and cheddar cheese, stirring to combine.
  • Once squash is fork tender, scoop stuffing into squash. Return to oven for 10-15 or until heated through. Enjoy!