Picadillo Stuffed Acorn Squash

Picadillo Stuffed Acorn Squash is a healthy, grain-free, and low carb option for a delicious and easy lunch or dinner.
Course Entree
Cuisine Cuban
Prep Time 10 minutes
Cook Time 1 hour
Total Time 1 hour 10 minutes
Servings 4 servings
Calories 349kcal
Author Karrie | Tasty Ever After


  • 2 acorn squashes , cut lengthwise and seeds removed
  • 1-2 tablespoons olive oil
  • 1 medium sized onion , chopped
  • 1 medium sized green or red bell pepper , chopped
  • 2 cloves garlic , minced
  • 1/2 teaspoon ground cumin
  • 1/4 teaspoon dried oregano
  • 1 pound lean ground beef (can substitute ground turkey or chicken)
  • 1/4 cup tomato paste
  • 1/4 cup dry sherry
  • 1/4 cup water
  • 1/2 cup pimiento-stuffed green olives , sliced
  • 1 tablespoon Worcestershire sauce
  • 1/2 teaspoon Tabasco sauce (optional)
  • salt to taste


  • Preheat oven to 375F/190C degrees.
  • Place acorn squash halves cut side down in a baking dish with 1/4 inch water. Cover with foil and bake 40-50 minutes or until tender.
  • 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.
  • Add tomato paste, sherry, water, sliced olives, Worcestershire sauce, and Tabasco to mixture. Combine well and cook for 10 minutes. Add salt to taste.
  • 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.  Serve immediately.


  • Store leftover picadillo in a tightly covered container in the refrigerator for 3-4 days or freeze up to 3 months


Calories: 349kcal | Carbohydrates: 32g | Protein: 27g | Fat: 12g | Saturated Fat: 3g | Cholesterol: 70mg | Sodium: 532mg | Potassium: 1453mg | Fiber: 5g | Sugar: 5g | Vitamin A: 2040IU | Vitamin C: 68.7mg | Calcium: 110mg | Iron: 5.4mg