Recipe: Picadillo Stuffed Squash

Recipe by: Ariel of

Picadillo squash (2)

Picadillo is a traditional dish in many of Latin America countries. It’s made with ground beef and other local ingredients.

I like the Cuban version that includes green olives to the mix of flavors. I also made it with 2 kinds of meat to make things more interesting: pork and beef.

Delicata winter squash is a striped long-shaped squash and is very common this time of the year in farmers markets and food grocery stores. Delicata is an ideal vessel to be stuffed with a meaty sauce like Picadillo because of its shape, not to mention that it is delicious by itself.


  • 3 Delicata winter squashes.
  • 1 pound ground beef
  • 1 pound ground pork
  • 5 tbs olive oil
  • 2 green bell-pepper, finely chopped
  • 1 big onion, finely chopped
  • 3 garlic cloves, minced
  • 2 fresh tomatoes chopped or 1 cup chopped canned tomatoes.
  • 1 tbs tomato paste
  • 5 cup white wine
  • 5 cup chicken or beef broth
  • 5 cup raisins
  • 5 cup pitted and chopped green olives
  • 2 bay leaves
  • 5 tsp dried oregano
  • 5 tsp ground cumin
  • 5 tsp ground cinnamon
  • 5 tsp fresh ground black pepper
    • 1tbs sherry vinegar



Start with the squash:

  • Preheat an oven to 400f
  • Cut each squash along side into 2 equal halves.
  • Spoon the seeds and pulp from inside so only the clean flesh remains.
  • Season each half with salt
  • Using 2tbs olive oil, brush the flesh of each squash half to cover completely with oil.
  • Put the squash halves in the oven, facing up, and bake until soft and lightly browned, about 30 minutes.


While the squashes are in the oven start preparing the Picadillo:

  • In a large pot, heat the remaining of the olive oil over medium-high heat.
  • Add the chopped bell-peppers, chopped onions, oregano, cumin, cinnamon and black pepper. lower the heat, and sauté for about 5 minutes until the vegetables are soft and starting to brown.
  • Add the minced garlic and sauté for another minute until fragrant.
  • Add the tomatoes, tomato paste, bay leaves, wine, broth, and sherry vinegar, add 1tsp salt, bring to a simmer and cook for 8-10 minutes until reducing the sauce in half.
  • Add the meat in golf ball-size chunks, Add the chopped olives and cover the pot. Cover and continue to simmer for another 20 minutes while stirring frequently until the meat is breaking up and cooked through.
  • Remove the cover and check – the picadillo suppose to be thick in texture but not dry. Reduce for another 3-4 minutes if necessary.
  • Fill each squash half with Picadillo.


  • Preheat an oven to 450f.
  • Drizzle 2 tbs olive oil on top of the stuffed squashes.
  • Put the stuffed squashes in a large baking tray and roast for 10-12 minutes. You want the meat on the top to be lightly browned but not scorched.


Picadillo squash (1)

Original Source: Recipe: Picadillo Stuffed Squash


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