Paleo Cranberry & Beef Stuffed Acorn Squash

Cranberry & Beef Stuffed Acorn Squash via StrictlyDelicious

Alternately titled “Christmas Stuffed Acorn Squash.”

I loooove happy accident recipes. And this is one of those dishes that happened completely by accident. It’s a result of one of those times where you look around your refrigerator/pantry/freezer and gather together the ingredients you have to make a meal.

In this case, I was looking to make work lunch for the week. I pulled together some seemingly random ingredients and ended up with this elegant, pretty, absolutely delicious meal that I will be making many more times before squash season is gone! I think this will be an amazing holiday dish too!!!

Cranberry & Beef Stuffed Acorn Squash via StrictlyDelicious

To my holiday loving soul, this stuffed acorn squash really does taste like Christmas. Or maybe it’s just a visual trick from the pretty red and green….

Either way, these flavors are incredible. Tender, fleshy, caramelized winter squash. Meaty ground beef sprinkled with anise flavor from the caraway and bursts of sweet-tart flavor from the dried cranberries. It’s all mixed together with mellow, savory browned garlic and piney rosemary.


Cranberry & Beef Stuffed Acorn Squash via StrictlyDelicious

Mmmm! I am so excited to share this with you!

Cranberry & Beef Stuffed Acorn Squash via StrictlyDelicious

Beef & Cranberry Stuffed Acorn Squash

Prep Time: 10 minutes

Cook Time: 40 minutes

Total Time: 50 minutes

Yield: 5 servings (as a light lunch or appetizer); ~2 servings (for very hungry people)


  • 1 large acorn squash
  • 1 1/2 teaspoon olive oil, plus some for brushing
  • 5 large garlic cloves, minced
  • 1/2 cup dried unsweetened cranberries
  • 1 teaspoon fresh rosemary, chopped
  • 1 pound ground beef
  • 1 teaspoon sea salt, plus some for sprinkling
  • 1/8 teaspoon ground black pepper {omit for AIP}
  • 1/2 teaspoon caraway {replace with 1 tsp ground ginger for AIP}


  1. Preheat the oven to 425 degrees F.
  2. Cut the top and the bottom off of the acorn squash, trying to cut off as little as possible. Carefully slice the acorn squash into 5 rings, cutting the acorn squash from side to side (not from top to bottom).
  3. Scrape the seeds and innards out of the rings and lay them flat on a baking sheet. Brush each ring with olive oil on both sides. Sprinkle sea salt over the top of the rings and place them in the preheated oven. Roast the squash rings for 30-35 minutes, flipping them over halfway through. The squash is done when it's lightly brown and fork tender.
  4. While the squash rings roast, heat the 1 1/2 teaspoons olive oil in a large skillet over medium heat. When the oil is hot, add the minced garlic and cook, stirring often until the garlic gets soft and is just starting to brown. Add the dried cranberries and chopped rosemary and cook for about 2 minutes more, until the rosemary is very fragrant and it smells like Christmas up in your kitchen.
  5. Remove the herb-cranberry mixture to a bowl and add the ground beef to the skillet. Cook the ground beef just until no pink remains, then drain any excess fat.
  6. Add the herb-cranberry mixture to the ground beef, as well as the 1 teaspoon salt, 1/8 teaspoon black pepper, and 1/2 teaspoon caraway. Stir to evenly combine.
  7. When the squash rings have finished roasting, remove the baking sheet from the oven. Spoon the beef-cranberry mixture into each ring and place back in the oven. Cook for 4-5 minutes more.
  8. Remove the baking sheet from the oven, top the stuffed squash with shredded parmesan cheese if desired, and enjoy!

Cranberry & Beef Stuffed Acorn Squash via StrictlyDelicious



    • says

      Hi Kellie, that doesn’t sound stupid at all. Great question! The skin on an acorn squash is actually so thin and tender that you don’t need to peel it off and can eat it right with the squash. I love that it saves me a step!

  1. says

    That looks lovely. I’ve never been terribly keen on squash and hate pumpkin, but I’m going to have to try this as it really does look delicious.

  2. says

    Maybe this is the solution to a problem: that of children who prefer not to eat those little yellow squashes. Or maybe they’ll just scoop the filling out and leave the veggie! Thank you so much for bringing it along. Happy FF.

  3. says

    I like the alternate name ‘Christmas stuffed’ 😀 Looks absolutely divine Lina!! I can imagine the explosion of flavors!! Wow!

  4. says

    Welcome to Fiesta Friday Lina, and thanks so much for bringing this artistic, flavorful squash to the party. The colors, the ingredients, the presentation, the photos are just so beautifully arranged. I’m sure the taste was amazing! So tell me, how do you focus on the one object and get everything blurry in the background? Is it the shutter speed?

  5. says

    Now this looks delicious, Lina! There is not one ingredient that I DON’T like in your recipe. <3 And you're right, it's quite appropriate for the holidays too…so pretty. In the meantime though, I think this is perfect for a fiesta…a Fiesta Friday! Thanks for sharing your recipe with the group…I, for one, am pinning this. 🙂