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Roasted Acorn Squash with Paleo Sausage Cranberry Stuffing

Pumpkin steals all the fall squash glory. Don’t get me wrong – I love pumpkin and can’t get enough of the pumpkin spice craze, but there are plenty of other squashes in the world. Quite honestly, some of them are tastier than pumpkin, just sadly ignored.

This roasted acorn squash with paleo sausage cranberry stuffing is my little attempt to cast some light on a delicious and frequently neglected vegetable.

The quantity of stuffing will easily fill 2 squash and, depending on their size, may fill 3. It’s also delicious on it’s own, though, so feel free to make it with 1 squash or none at all!

roasted stuffed acord squash

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I highly recommend taking the time to plump the dried cranberries.

To do this, pour about a cup of hot water or, for lots of extra flavor, hot apple cider, over the cranberries and let them sit for about five minutes. You’ll be amazed by how much liquid they soak up! Drain the cranberries before adding them to the stuffing.

What makes this stuffing ‘paleo’ is subbing in cauliflower instead of bread crumbs.

This is more successful when you don’t just use cauliflower florets whole. Instead, use ‘riced’ cauliflower.  

You can ‘rice’ cauliflower several different ways.

Probably the easiest way is with a grating disc in a food processor, but if you’re like me and don’t currently have a food processor, chop the (raw) cauliflower with a large knife. You can also use the coarse side of a traditional box grater!

Roasted Acorn Squash with Paleo Stuffing
As noted in the recipe, you can fill multiple acorn squash, or you can use the filling, alone, as a tasty meal. To make this easier to prepare, cook the acorn squash ahead of time by a few hours, or even the previous day, cover it tightly, and then cook up the stuffing and roast the squash a second time when you’re ready to eat!

Roasted Acorn Squash with Paleo Sausage Cranberry Stuffing

Roasted Acorn Squash with Paleo Sausage Cranberry Stuffing
Cook Time 1 hour
Total Time 1 hour


  • 2 acorn squash (you can use just 1 but you'll have extra stuffing)
  • 1 pound of bulk mild or sweet Italian sausage
  • 1 tablespoon of almond or olive oil
  • 1/2 an onion, chopped fine
  • 1 cup of cauliflower, riced
  • 1/2 cup of non sweetened dried cranberries, plumped
  • 1 apple, cored and chopped roughly
  • 1 tablespoon of fresh, minced thyme leaves
  • 1 tablespoon of oregano
  • Salt and pepper to taste


  1. Begin by pre-roasting the acorn squash. First, preheat your oven to 450 degrees Fahrenheit.
  2. Cut your acorn squash in half, from pole to pole, and scoop out the seeds/stringy bits (just like you're cleaning out a pumpkin). You can either cut off the stem or just cut slightly to one side of it.
  3. Place the squash, cut side up, in a rimmed baking dish (I like to use a metal 9x13 pan) and add about two cups of water before loosely covering the dish with foil.
  4. Roast until the quash is starting to become tender, but is not mushy, about 25 minutes. When you remove the squash from the oven, discard the water.
  5. While the squash is roasting, heat about a tablespoon of oil in a large pan over medium-high heat. When it is warm and shimmering, add the onions and sauté, stirring frequently, until they are semi-translucent.
  6. Add the sausage and cook, stirring occasionally, until it is thoroughly browned, 5-7 minutes.
  7. Add the cauliflower, apple, dried cranberries, thyme, oregano, salt, and pepper and continue cooking until the sausage is thoroughly cooked and no longer pink.
  8. When the stuffing and squash are both ready, fill the squash halves with the stuffing and mound it, as much as is reasonable.
  9. Return the squash (in the baking dish!) to the oven and cook uncovered for an additional 20-25 minutes, or until the squash's edges are browned and tasty looking. To ensure a nice browned edge, brush the squash with melted butter and brown sugar or maple syrup before putting it back in the oven. This is optional, but tasty!
  10. Serve and enjoy!
Roasted Acorn Squash with Cranberry Sausage Stuffing

Looking for more Paleo recipes?

Oven roasted fall veggies and sausage

Paleo Oven Roasted Fall Vegetables and Sausage

Oven “fried” plantains

Baked Sweet Plantains - Healthier Platanos Maduros

watercolor luna moth with crystals and the text "Natasha" of The Artisan Life

{ 26 comments… add one }
  • Jill March 17, 2018, 06:59

    Do you think this could be made with fresh or frozen cranberries?
    I always stock up for the freezer around the holidays.

    Thanks for any ideas you may have!

    • Natasha March 17, 2018, 08:57

      I don’t see why that wouldn’t work just fine! I know my mom makes “regular” stuffing with fresh cranberries so I’d expect it to work here, too.

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