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Sausage, Cranberry, And Pine Nut Stuffed Winter Squash

I just love fall and winter squash. There is so much variety, and I just love the flavor. I was inspired to make this dish while I was at the grocery store alone and got so excited! I’ve been venturing more into exploring different flavor combinations and taking baby steps into trying them. I decided to try mixing sweet and savory in a sausage, cranberry, and pine nut stuffed winter squash. What I love about this dish is that it is as flavorful as it is pretty.

How To Make It

I took my acorn squash and cut them in half width wise and it’s so pretty that way! I cut off the pointed bottoms so they can sit evenly on the baking sheet. I had a couple where that caused a hole in the bottom, that’s totally okay! Then I light coated the flesh with olive oil and salt, turned bowl side down onto the baking sheet and roasted for 20 minutes at 425 degrees. This allowed for the squash to roast and steam without drying out.

While that is roasting, I toasted the pine nuts then set them aside. In my food processor I processed the kale into extremely small pieces. If you do not have a food processor, then hand chop into smallest pieces you can. I then browned the sausage in the pan I roasted the pine nuts in. (Less dishes!) After about 7 minutes, I added in the onions and cooked for another 5 minutes. Next I removed from the heat and stirred in the cranberries, pine nuts, salt, and kale.

After the 20-25 minutes of roasting, I took the squash out of the oven, used tongs and flipped them over so I could stuff the bowls with my meat mixture. For the squashes that have holes in the bottom, tear off a piece of a leaf of kale and cover the hole. It works surprisingly well! After this I placed the stuffed squash back into the oven to cook for another 15 minutes.

It’s truly a simple dish that looks and tastes fancy. It is also gluten free, grain free, dairy free, and nut free.

sausage cranberry pine nut stuffed squash road to living whole

More great squash recipes:

vegan paleo stuffed squash
Vegan Stuffed Winter Squash
grain free paleo gluten free kale and sausage stuffed acorn squash
Kale and Sausage Stuffed Winter Squash
Sausage Cranberry Pine Nut Stuffed Acorn Squash

Sausage, Cranberry, And Pine Nut Stuffed Winter Squash

Prep Time 15 minutes
Cook Time 40 minutes
Total Time 55 minutes
Servings 6 servings


  • 6 acorn squash
  • 1 lb sweet italian ground sausage
  • 3 stalks curly kale Plus one more for covering holes in the squash
  • 1 medium yellow onion
  • 3/4 cup dried cranberries
  • 1/2 cup pine nuts
  • 2 tbsp extra virgin olive oil (EVOO)
  • 1/2 tsp salt


  • Preheat oven to 425 degrees.
  • Cut your acorn squash in half width wise and using a spoon, scoop out all seeds and strings. Then cut off the pointed bottoms of the bottom halves. These need to lay flat on the baking sheet.
  • Coat lightly with olive oil and salt, place bowl side down on your baking sheet. Place in the oven and bake for 25 minutes.
  • In a large skillet, lightly toast pine nuts. Set aside.
  • Finely dice onions and in your food processor, process kale into extremely small pieces. If you do not have a food processor, hand chop as fine as you possibly can.
  • On medium heat, cook sausage. Add in diced onions and cook an additional 5 minutes. Turn off heat and add cranberries, toasted pine nuts, kale, and salt. Mix well.
  • Remove squash from the oven and use tongs to flip over. If some of the squash have holes in the bottom from cutting off the bottom, lay a raw kale leaf in the bottom to close that up.
  • Scoop sausage mixture into each half of squash, feel free to overfill.
  • Bake for another 15 minutes.
  • Remove from the oven and enjoy!



6 thoughts on “Sausage, Cranberry, And Pine Nut Stuffed Winter Squash”

  1. Marian, this looks delicious! I love pine nuts – not so sure about the sausage – but I bet if you’re a meat eater it is amazing. It seems like I could make it without the sausage – but I’d want to replace it with something around that consistency – probably enough fat in the pine nuts? Thanks – I’m going to try it for sure.

  2. Ooolala…you may just find this as a side dish at my Thanksgiving table. Love the little kale leak tip!!

    I wish recipes just came to me when I’m in the grocery store…I have to plan and shop off of a list…or else I am lost!

    Thanks for the recipe and the picture is beautiful!

  3. This sounds delicious I may change up some of the ingredients for things we can get here and repost on my blog and link back to you if that’s ok… Thanks for sharing

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Hi friend!

I’m Marian Mitchell, Health Coach, Chronic Illness Warrior, Mom, and Food Lover. I help you navigate the food and lifestyle side of Chronic Disease Management with coaching, meal plans, recipes, podcast, and this blog. You can thrive without eating the same 4 things every day. I’m here to show you how.

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