Stuffed Acorn Squash with Sausage, Apples and Cranberries

This stuffed acorn squash with sausage, apples and cranberries is packed with all the best savory-sweet fall flavors! Tender roasted acorn squash is filled with savory sausage, apples, dried cranberries, pecans, vegetables and fresh herbs for a cozy, satisfying meal. It’s naturally gluten free and paleo, easy to make Whole30 compatible, and perfect for everything from a weeknight fall dinner to a holiday meal!

*Recipe update: This recipe was originally published in 2017 and has been updated with new photos and a slightly simplified method. The sausage, apple and cranberry filling you love is still the star of the recipe.

Once fall squash season begins, stuffed acorn squash is one of those meals I always come back to. Acorn squash has the perfect natural shape for stuffing, and roasting it brings out its sweetness while creating those caramelized golden edges.

For this version, the filling has everything I want in a fall dinner: savory sausage, onion and celery, crisp apples, cranberries, pecans and plenty of fresh herbs.

The combination is a little sweet, a little savory, hearty without feeling too heavy, and it works just as well for an everyday dinner as it does alongside your favorite Thanksgiving recipes.

I also streamlined the original method a bit. The sausage, onion and celery can all cook in the same skillet, and there’s no need for extra steps or dishes. While the squash roasts, you can make the entire filling.

Why You’ll Love This Sausage Stuffed Acorn Squash

• Perfect savory-sweet combination. Sausage and herbs balance the naturally sweet squash, apples and cranberries.
• Made with simple whole-food ingredients. It’s naturally gluten free, dairy free and paleo.
• Easy to make Whole30 compatible. Just use compatible sausage and dried cranberries.
• Great for fall entertaining. The stuffed squash halves look impressive without being difficult to make.
• Most of the cooking happens at the same time. Make the sausage filling while the squash roasts.
• Easy to prep ahead. Both the squash and filling can be prepared in advance.

Ingredients You’ll Need

Acorn Squash

Look for small to medium acorn squash that feel heavy for their size and don’t have soft spots.

Smaller squash work especially well here because each half makes a nice individual portion. Roasting them cut-side down gives you tender flesh with beautifully browned, caramelized edges.

Pork Sausage

I like bulk pork sausage for this recipe because it gives the filling so much flavor without requiring a long list of additional seasonings.

Italian sausage works well, or you can use a milder breakfast-style pork sausage. For Whole30, make sure you’re using a compatible sausage with no added sugar or other non-compatible ingredients.

Apples

Use an apple that holds its shape well when cooked. Pink Lady, Honeycrisp or Granny Smith are all great choices.

I like cutting the apple into roughly 1/3-inch pieces rather than a very fine dice. You still get distinct pieces of apple in every bite, and they add great texture and color to the finished filling.

Onion, Celery and Garlic

These give the filling that classic savory stuffing flavor and balance the sweetness from the squash and fruit.

Fresh Herbs

A combination of sage, thyme and rosemary gives this stuffed squash its cozy fall flavor.

I’ve slightly reduced the amount of herbs compared with the original version so they complement the sausage and apples rather than overpowering them.

Dried Cranberries

Dried cranberries provide little bursts of tart-sweet flavor throughout the stuffing.

For Whole30, choose compatible dried cranberries without added sweeteners.

Pecans

Chopped pecans add crunch and a rich, nutty flavor. You can toast them first if you want an even deeper flavor, but it isn’t necessary for this recipe.

How to Make Stuffed Acorn Squash

Roast the Acorn Squash

Preheat your oven to 425°F and line a large baking sheet with parchment paper.

Carefully cut each squash in half lengthwise, then scoop out the seeds and stringy center with a spoon.

Brush the cut sides lightly with oil and season with sea salt and black pepper. Arrange the halves cut-side down on the baking sheet.

Roast for about 25–35 minutes, depending on the size of your squash. They’re ready when the flesh is tender when pierced with a fork but the squash halves still hold their shape.

Make the Sausage Apple Filling

While the squash roasts, heat a large skillet over medium-high heat.

Add the sausage and cook, breaking it into bite-size crumbles as it browns.

Once the sausage is mostly cooked through, add the diced onion and celery right to the skillet. Cook everything together for several minutes until the vegetables begin to soften.

Add the garlic, apples and fresh herbs and cook for another 2–3 minutes. You want the apples to soften slightly without becoming mushy.

Stir in the cranberries and pecans and cook for another minute.

Taste the filling before adding extra salt—the amount you’ll need will depend on the sausage you’re using.

Stuff and Finish the Squash

Once the squash is tender, carefully flip each half cut-side up.

Spoon the sausage mixture generously into the squash halves, piling it up in the centers.

Return the stuffed squash to the oven for about 5 minutes so everything is hot together.

For those extra browned, crispy bits on top, you can broil the stuffed squash for 1–2 minutes at the end. Just watch closely since it can brown quickly.

Finish with fresh chopped parsley and serve warm.

Tips for the Best Stuffed Acorn Squash

Don’t over-roast the squash. It should be completely tender, but you still want the skin and flesh firm enough to support the filling.

Keep the apple pieces fairly chunky. If they’re diced too small, they can disappear into the sausage mixture. About 1/3-inch pieces give you the best texture.

Don’t automatically add extra oil to the skillet. Pork sausage usually releases enough fat to cook the onion and celery. Add a little oil only if the pan looks dry.

Taste before seasoning. Sausage varies considerably in saltiness, so it’s better to season the filling at the end.

Don’t overcook the apples. A few minutes is enough. They should be tender-crisp rather than soft like pie filling.

Can I Use Dried Herbs?

Yes. Fresh herbs give you the best flavor here, but dried herbs work when needed.

For the fresh herbs in this recipe, substitute approximately:

1 teaspoon dried sage + 1/2 teaspoon dried thyme + 1/2 teaspoon dried rosemary.

I wouldn’t use a full teaspoon of each dried herb because dried herbs are much more concentrated, particularly rosemary.

Can I Make This Stuffed Squash Whole30?

Yes, the recipe is easy to make Whole30 compatible!

The two ingredients you’ll want to check carefully are the sausage and dried cranberries. Choose varieties that meet your Whole30 needs.

Everything else in the recipe is naturally compatible.

Can I Make Stuffed Acorn Squash Ahead of Time?

Definitely, and this is one of the reasons it’s a nice option for a holiday meal.

You can roast the squash and prepare the entire sausage filling up to one day ahead. Store them separately in airtight containers in the refrigerator.

When you’re ready to serve, arrange the squash cut-side up on a baking sheet, fill them with the sausage mixture and bake at 400°F until heated through.

You can broil them briefly at the end for the freshly browned look.

How to Store Leftovers

Store leftover stuffed squash in an airtight container in the refrigerator for up to about 4 days.

For the best texture, reheat it in a 375–400°F oven until warmed through. You can also use the microwave for individual portions.

This sausage stuffed acorn squash is one of those recipes that feels like fall in every bite. The combination of savory sausage, sweet apples and cranberries, fresh herbs and tender roasted squash makes it cozy enough for a weekend dinner but easy enough for a weeknight. It’s also a great make-ahead option for entertaining or the holidays.

I hope you love this updated version as much as I do! If you make it, be sure to leave a rating and comment below so I know how it turned out!

More Fall Dinner Recipes You’ll Love

• Sausage Stuffed Butternut Squash
• Harvest Casserole 
• Paleo Butternut Sausage Stuffing with Apples & Cranberries 
• Maple Roasted Butternut Squash with Brussels Sprouts and Bacon
• Butternut Squash Chicken Chili 
• Creamy Chicken Potato Casserole

Stuffed Acorn Squash with Sausage, Apples and Cranberries

This roasted stuffed acorn squash is filled with savory sausage, apples, cranberries, pecans, onion, celery and fresh herbs. It's packed with sweet and savory fall flavor and makes a delicious weeknight dinner or holiday meal. Paleo, gluten free and easy to make Whole30 compatible.

Author: Michele

Prep Time: 15 minutes

Cook Time: 40 minutes

Total Time: 1 hour 55 minutes

Course: Anytime, Dinner, Holiday, Holiday Side Dish

Cuisine: Gluten-free, Paleo, Whole30

Servings: 4 servings

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4.82 from 64 votes

Ingredients

• 2 medium acorn squash
• 1 tablespoon olive oil or avocado oil divided, plus more if needed
• Sea salt and black pepper
• 1 lb bulk pork sausage
• 1 small yellow onion diced
• 2 celery stalks diced
• 2 cloves garlic minced
• 1 small crisp apple diced, such as Pink Lady, Honeycrisp or Granny Smith
• 1 tablespoon chopped fresh sage
• 1 teaspoon fresh thyme leaves
• 1 teaspoon chopped fresh rosemary
• 1/3 cup dried cranberries
• 1/3 cup chopped raw pecans
• Fresh chopped parsley for garnish, optional

Instructions

1. Preheat your oven to 425°F and line a large baking sheet with parchment paper.
2. Cut each acorn squash in half lengthwise and scoop out the seeds and stringy center.
3. Brush the cut sides of the squash lightly with about 2 teaspoons of the oil and season with sea salt and black pepper. Arrange the squash halves cut-side down on the prepared baking sheet.
4. Roast for 25–35 minutes, depending on the size of the squash, or until the flesh is tender when pierced with a fork.
5. While the squash roasts, prepare the filling. Heat a large skillet over medium-high heat. Add the sausage and cook, breaking it into crumbles as it browns.
6. Once the sausage is mostly browned, add the onion and celery directly to the skillet. Cook for 3–4 minutes, stirring occasionally, until the vegetables begin to soften. Add the remaining oil only if the skillet seems dry.
7. Add the garlic, diced apple, sage, thyme and rosemary. Season with black pepper and sea salt as needed. Cook for another 2–3 minutes, until the apple begins to soften but still holds its shape.
8. Stir in the dried cranberries and pecans and cook for about 1 minute, then remove the skillet from the heat.
9. Turn the roasted squash halves cut-side up. Divide the sausage mixture among the four halves, piling it generously into the centers.
10. Return the stuffed squash to the oven for about 5 minutes, until everything is heated through. For a more browned top, broil for another 1–2 minutes, watching closely.
11. Garnish with fresh parsley if desired and serve warm.

Recipe Notes

Dried herbs: Substitute about 1 teaspoon dried sage, 1/2 teaspoon dried thyme and 1/2 teaspoon dried rosemary.

Whole30: Use compatible sausage and dried cranberries.

Make ahead: Roast the squash and prepare the filling up to one day ahead. Refrigerate separately, then stuff and bake at 400°F until heated through.

Apples: Pink Lady, Honeycrisp and Granny Smith all work well. Cut the apple into roughly 1/3-inch pieces so it maintains some texture during cooking.

Nutrition

Calories: 365kcal

Carbohydrates: 26g

Protein: 14g

Fat: 23g

Saturated Fat: 8g

Cholesterol: 54mg

Sodium: 58mg

Potassium: 814mg

Fiber: 4g

Sugar: 8g

Vitamin A: 660IU

Vitamin C: 20.3mg

Calcium: 76mg

Iron: 2.1mg

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