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Roasted Acorn Squash with Paleo Sausage Cranberry Stuffing

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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 oft-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!

Acorn Squash With Paleo Sausage Cranberry StuffingI 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 find affordable food mills/ricers. It doesn’t need to be exactly as small as rice, but the smaller the better. Only cut the florets, not the stalks.

Roasted Acorn Squash with Paleo Stuffing

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Roasted Acorn Squash with Paleo Sausage Cranberry Stuffing
Cook time: 
Total time: 
Serves: 4
  • 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
  • ½ an onion, chopped fine
  • 1 cup of cauliflower, riced
  • ½ 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!

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 Cranberry Sausage Stuffing

What’s your favorite squash to eat? How do you like to prepare it?

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

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{ 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.

  • MyRuca2014 December 6, 2017, 10:53

    I really like this recipe! It’s so flavourful and comforting. It feels like my stomach is getting a nice hug when I eat it. It’s a favourite in our family for sure.

    • Natasha December 6, 2017, 10:56

      I’m so glad and thank you!

  • t December 21, 2015, 11:23

    I have made this a few times and we love it. Question can I make it ahead I want to serve it on Christmas eve but we will be gone and will not have time to make it.

    • Natashalh December 21, 2015, 17:14

      I’m so glad you like my recipe! That nice, fresh out of the oven browning is something that works so well for this dish, so it’s not a perfect make ahead candidate. It should be possible to mostly make it ahead and then just do the final 25 minutes or so of roasting right before serving. I’d cook all the ingredients ahead and store them separately in the fridge, then mix them together and reheat/brown in the oven right before serving. I hope you have time for that and you enjoy! If you like making food ahead, I’ll be wiring an e-book on meal prep soon so stay tuned. =)

  • Heather l. December 8, 2014, 17:08

    Making this for the second time tonight…love this recipe & it is just amazing as leftovers! I had to stop myself from eating the extra stuffing so I have room for the squash goodness!

    • natashalh December 9, 2014, 07:11

      That’s so awesome! I’m glad you like it. Thanks for letting me know! Comments like yours really make my day. =)

  • Lisa @ Cooking with Curls November 8, 2014, 19:22

    I love the idea of cauliflower in place of the bread! I need to try different types of squash, these look really delicious!!

    • natashalh December 19, 2014, 08:00

      Cauliflower in lieu of bread certainly does cut down on carbs! Sorry my reply is a little late – my anti-spam plugin went a little crazy lately and stuck a bunch of non-spam over in the spam folder.

  • sue October 20, 2014, 07:44

    Hi there
    just wanted to let you know I found this recipe on Pinterest. I made it yesterday and loved it!
    I’m not a fan of cauliflower so I subsititued white mushrooms. I sautéed them with the apples then added to recipe. Delicious! thank you Sue

    • natashalh October 20, 2014, 07:46

      That’s awesome! Thank you for letting me know. I guess we’re opposites – mushrooms are just about the only food I really don’t like! Thanks so much for stopping by. =)

  • rlk @ FirstTimeFoods November 28, 2013, 13:01

    Hi Natasha! Stopping by from the Saturday Night Fever link-up. Don’t you just love how the acorn squash is its own little bowl? It’s definitely my favorite fall squash. I’ve made various stuffed acorn squash (a ‘southwest’ style with ground turkey and beans is my favorite), but I like your idea of using cauliflower, and the apples and cranberries are a nice touch! Thanks for sharing!

    • natashalh December 3, 2013, 08:43

      The cauliflower really works well as a bread substituted. It ends up soaking up the flavor and tastes more like sausage than cauliflower! Thanks so much for stopping by. =)

  • Jen Nikolaus November 27, 2013, 01:38

    This is a beautiful side dish! I love the colors and that you used cauliflower instead of bread. What a great idea and super healthy! Thanks for sharing on Saturday Night Fever! Pinned!

    • natashalh November 27, 2013, 06:57

      Thank you for stopping by! I’m always looking for ways to sneak a little extra healthy into a meal without making it taste that different, you know? It’s a good way to trick people. =)

  • CJ Huang November 26, 2013, 18:39

    Your stuffing’s got loads of yum! Great idea with soaking the cranberries in apple cider too. 🙂

    • natashalh November 26, 2013, 19:09

      That makes them so super delicious! I really like how well the cauliflower substitutes for bread crumbs in this – it really tastes like everything else and not cauliflower. Thanks so much for stopping in!

  • Heather @ Sugar Dish Me November 24, 2013, 10:22

    Yummmm! You are right about squash rivaling pumpkin. Butternut is my favorite, only followed by Acorn because they are majorly annoying to peel. This recipe is beautiful. Love the cauliflower in place of bread!!!

    • natashalh November 24, 2013, 10:43

      That’s why I didn’t bother to peel it! So much easier. When you cut the cauliflower up, it doesn’t really seem like you’re eating cauliflower. It seemed like a great way to subtract unneeded carbs and add some vitamins!

  • Tammy November 23, 2013, 14:33

    Hi Natasha, Thank you so much for stopping by and commenting. You have a really wonderful site here.
    I’ve discovered a whole new love for squash this winter…I’ve been making it quite a bit lately. This looks so good with that stuffing..a very warm and comforting holiday dish.

    Have a wonderful weekend 🙂


    • natashalh November 23, 2013, 15:04

      Thank you so much, Tammy! I mostly write this blog because it’s fun. I like challenging myself to take better pictures and find the best way to describe a process! I really enjoyed eating this roasted squash other week, but I also have to admit I’m looking forward to some more traditional stuffing later this week!

  • Katerina November 22, 2013, 07:11

    Squash used to be very spurned here in Greece but this has started to change lately! These are deliciously stuffed squashes!

    • natashalh November 22, 2013, 07:22

      I had no idea! That’s very interesting. I know corn isn’t as popular in Europe as it is in America, either. Things like that fascinate me! Thank you for stopping by and sharing.

  • Susan Zutautas November 22, 2013, 06:12

    Lately my favorite squash is sweet potatoes but your acorn squash is looking pretty delicious. Everything you’ve stuffed it with I like. I have a hard time getting my husband to eat acorn but I’m sure he’ll like it when serve it to him using your recipe.

    • natashalh November 22, 2013, 07:22

      I hope y’all enjoy! The stuffing is good for stuffing just about anything and it isn’t packed full of bread.

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