Kalyn's Kitchen

Easy Roasted Winter Squash and Sausage with Herbs

Easy Roasted Winter Squash with Sausage and Herbs is a perfect dinner for a cold fall or winter night and this dinner is low-glycemic, gluten-free (with gluten-free sausage) and dairy-free! Use Sheet Pan Meals for more dinners like this one.

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Easy Roasted Winter Squash and Sausage with Herbs found on KalynsKitchen.com

Winter squash is one of those perfect vegetables that’s easy to grow, nutritious, and versatile, and when it’s roasted into caramelized goodness like this Easy Roasted Winter Squash with Sausage with Herbs, I think it’s one of the best-tasting foods in the world.I never liked squash as a kid, but by my late twenties my Grandma Denny taught me to like butternut squash that she’d roast in a hot oven, then mash with lots of butter, salt, and pepper.

That’s a recipe you can’t go wrong with, but the last few years I’ve been roasting squash with olive oil, and every version I’ve tried has been a winner, including this dish of squash roasted with Italian sausage and herbs. I made this with my favorite turkey Italian Sausage; use any type of winter squash you prefer for this tasty dinner.

Easy Roasted Winter Squash and Sausage with Herbs found on KalynsKitchen.com

My neighbor Brooke gave me this Jarrahdale squash that she’d grown in her garden. I was excited to try out a new variety of squash, and definitely I’m planning to grow this myself next year. (Thanks Brooke!) I wanted to use cubes of squash for this recipe, and I started by using a sharp spoon to scoop out the seeds. This piece of squash with the skin weighed just over 2 pounds. When I’m going to peel and cut up a butternut squash, I use a sharp vegetable peeler to remove the skin, but that wasn’t going to work with this squash due to the ridges. When the seeds were gone, I cut the squash into slices around two inches thick. Then I used a very sharp knife to carefully peel away the skin on each slice of squash. When all the squash was peeled, I cut it into pieces, trying to keep them close to the same size.

I tossed the pieces with olive oil, salt and pepper, and herbs and started roasting the squash. (Next time I’d use a baking sheet!) I’ve made this twice and used sage one time and rosemary the next for the fresh herbs, and I think there are a few other types that would also work. I was using uncooked turkey Italian sausage, so while the squash started to roast, I poked holes in the sausage with a fork and pre-cooked it until the microwave until it was firm enough to cut into even slices. After the sausage cools for a few minutes, cut into slices about 3/4 inches wide. The sausage will not look browned at all at this point.

After the squash has roasted for 20 minutes, stir it and spread out evenly in the dish, then lay sausage pieces in a single layer on top of the squash. Roast for about 20 minutes, or until one side of the sausage pieces has browned. Then use a fork to carefully turn the sausage so the other side is facing up and roast for 10-20 minutes more, until all the sausage pieces are nicely browned and squash is slightly caramelized on the bottom. Devour.

Easy Roasted Winter Squash and Sausage with Herbs found on KalynsKitchen.com

More Roasted Winter Squash to Try:

Agave and Balsamic Glazed and Roasted Buttercup Squash from Kalyn’s Kitchen
Roasted Butternut Squash and Onion Lasagna from One Hot Stove
Roasted Butternut Squash with Moroccan Spices from Kalyn’s Kitchen
Honey Roasted Acorn Squash from Joy the Baker
Cheesy Sausage and Pepper Stuffed Acorn Squash from Kalyn’s Kitchen

Easy Roasted Winter Squash and Sausage with Herbs

Easy Roasted Winter Squash with Sausage and Herbs is a perfect dinner for a cold fall or winter night.


  • 2 lbs. winter squash cubes (use any type of winter squash, choosing a piece that’s just over 2 lbs.)
  • 4-5 sweet turkey Italian sausage (I would not use pork sausage for this.)
  • 2 T olive oil
  • 1/2 tsp. dried thyme (or more)
  • salt and fresh ground black pepper to taste
  • 1-2 T chopped fresh herbs of your choice (I’ve tried sage and rosemary, could also use thyme, marjoram, or oregano. You could also use a bit more dried thyme if you don’t have fresh herbs.)


  1. Preheat oven to 400F/200C and spray a flat glass or crockery baking dish with olive oil or non-stick spray.
  2. I used a dish that was 9″ X 12″ because I was baking it in my toaster oven, but I recommend using a sheet pan for this dinner.
  3. Cut squash in half if needed, and use a sharp spoon to scrape seeds and stringy insides from the squash.
  4. If it’s a smooth skinned squash like butternut, you can peel off the skin with a vegetable peeler.
  5. For rough skinned squash or squash with ridges, cut into slices about 2 inches wide, then use a sharp knife to cut the skin away from each slice.
  6. Cut squash into uniformly-sized pieces.
  7. Put squash in a bowl, then toss with olive oil, dried thyme, salt and fresh ground black pepper and chopped fresh herbs, if using. (I would use about 1 tsp. dried thyme if I wasn’t using fresh herbs.)
  8. Arrange squash cubes in an even layer in the baking dish and start to roast.
  9. While you’re cutting up squash, put turkey Italian sausage on a plate, poke holes on each side of the sausages, and microwave on high for about 4-5 minutes (or until sausage is firm enough to cut into even slices.)
  10. Remove sausage from microwave and let cool.
  11. When it’s cool enough to handle, cut the sausage into slices about 3/4 inch wide.
  12. After squash has cooked for 20 minutes, stir squash, spread back out into the dish in an even layer, then arrange sausage slices on top of squash and roast 20 minutes more, or until sausage pieces are starting to brown.
  13. Then use a fork to carefully turn each piece of sausage so the other side is facing up and roast 10-20 minutes more, until sausage is browned and squash is slightly browned on top and caramelized on the bottom.
  14. Serve hot.
  15. In many dishes pork or turkey Italian sausage can be used interchangeably, but in this case I think the fat that would drip down from the pork sausage would make the squash much too greasy. Look for turkey Italian sausage near the ground turkey in your supermarket.


This recipe created by Kalyn.

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Low-Carb Diet / Low-Glycemic Diet / South Beach Diet Suggestions:
Turkey Italian sausage is a great choice for any phase of the South Beach Diet, but using winter squash makes this Easy Roasted Winter Squash with Sausage and Herbs something to eat for phase 2 or 3 for South Beach. It’s also good for other low-glycemic diet plans, but winter squash is too high in carbs for a low-carb diet.

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Nutritional Information?
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    52 Comments on “Easy Roasted Winter Squash and Sausage with Herbs”

  1. Buying fresh herbs feels like such a splurge here this time of year, but I'm so glad I did; I think they really made the dish. Great recipe.

  2. Made this for dinner using acorn squash and precooked apple chicken sausage. My husband loved it, and he's not usually a squash guy. Added some garlic powder and onion powder. We devoured this. Even the drippings/caramelization on the dish were amazing sopped up with dinner rolls!

  3. So glad you liked it! I just bought some winter squash at the market here too.

  4. We love this, just tried with butternut squash and some polish sausage. I added a few red potatoes and some purple onion and fresh parsley. Squash is just coming into season here in NC.

  5. So glad you liked it!

  6. I just tried this recipe, I used Acorn squash and only had parsley. Fabulous! First time I've cooked acorn squash or turkey sausage. My husband and I both loved this simple and tasty recipe.
    Thank you so much!

  7. Debbie, so glad you liked it.

  8. I (finally!) made this tonight for dinner, although I cut the portions in half. I ate it fresh out of the oven on a bed of spinach – the heat from the still piping hot butternut squash and sausage was just enough to barely wilt the spinach. Delicious!

  9. Umm this looks delicious and healthy. Thanks for the share! My husband is a health nut so I think he will like this recipe.