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Challenge: Healthy Swaps

Picadillo Stuffed Acorn Squash

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Healthy, grain-free, and low carb, makes this Cuban picadillo stuffed squash an easy and tasty option for lunch or dinner.

Picadillo Stuffed Acorn Squash

  • Servings: half stuffed squash
  • Yield: 4
  • Prep Time: 10 min
  • Cooking Time: 1 hr


  • 2 acorn squashes, cut lengthwise and seeds removed
  • 1-2 Tb olive oil
  • 1 medium sized onion, chopped
  • 1 medium sized green or red bell pepper, chopped
  • 2 cloves garlic, minced
  • ½ tsp ground cumin
  • ¼ tsp dried oregano
  • 1 pound lean ground beef, turkey, or chicken
  • ¼ cup tomato paste
  • ¼ cup dry sherry
  • ¼ cup water
  • ½ cup pimiento-stuffed green olives, sliced
  • 1 Tb Worcestershire sauce
  • ½ tsp Tabasco sauce, optiona
  • salt to taste


  1. Preheat oven to 375. Place acorn squash halves cut side down in a baking dish with ¼ inch water. Cover with foil and bake 40-50 minutes or until tender.
  2. While the squash is roasting, prepare the picadillo filling (this can also be made the day before). Place olive oil in large skillet over medium heat. Sauté onions, green pepper, and garlic for 5 minutes or until tender. Add cumin and oregano and sauté another 1-2 minutes. Add ground beef, turkey, or chicken and cook together with vegetables for 10 minutes or until lightly browned and cooked through.
  3. Add tomato paste, sherry, water, sliced olives, Worcestershire sauce, and Tabasco to mixture. Combine well and cook for 10 minutes. Add salt to taste.
  4. Remove acorn squash halves from oven and fill with picadillo mixture. Place back in oven and bake for 10-15 minutes until squash is fully cooked throughout.

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