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Stuffed Delicata Squash with Cranberry Apple Pork Stuffing

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Stuffed delicata squash is simply roasted to sweeten and caramelize and then stuffed with a delicious mixture of seasonal fall ingredients like ground pork, cranberries, apples, leeks and fennel. It’s an easy meal packed with flavor and impressive enough for a special occasion.

Stuffed delicata squash is simply roasted to sweeten and caramelize and then stuffed with a delicious mixture of seasonal fall ingredients like ground pork, cranberries, apples, leeks and fennel.

When I’m not just simply roasting buttercup squash and eating it that way, stuffing winter squash full of deliciousness is my next go-to for easy fall dinners.

And this recipe for stuffed delicata squash is definitely stuffed full of deliciousness.

With fall-centric ingredients like cranberries, apples, fennel and leeks rounding out some ground pork (or Italian sausage), these roasted delicata boats are the perfect balance of savory and sweet.

One of the reasons I love stuffing delicata squash is its edible skin.

Unlike stuffing spaghetti or butternut, there’s no need to dig the flesh out from the skin, you can just cut it up and enjoy each forkful!

Of course, that’s in addition to its delicious slightly sweet caramelized flavor that develops when you roast it. Just like roasted koginut squash.

If I’m not making delicata squash soup, I’m most definitely roasting it to enjoy that perfect sweet winter squash flavor.

Check out my guide to winter squash for lots more info on all the squash in season right now!

Oven roasted delicata squash cut in halves before stuffing.

Another great feature of delicata squash is its size.

Because it tends to be on the smaller side (I grew these in my garden this year and they were about length of my hand from wrist to fingertip), delicata roasts quickly.

Achieving fork tender flesh is possible in almost half the time of a larger variety squash.

You know what that means? It’s the perfect choice for weeknight dinners!

The 25-30 minutes it takes to roast the delicata gives you the perfect amount of time to prep and cook the stuffing.

So, once the squash comes out of the oven, just spoon the stuffing into each half and dinner is served!

An easy filling of ground pork, cranberries, apples, leeks and fennel in the pan before stuffing the roasted delicata squash.

DELICATA SQUASH STUFFING

Since delicata is in season right as fall rolls around, I wanted to keep that seasonal vibe with the stuffing ingredients.

Ground pork/Italian sausage – used as the protein base. You can either use plain ground pork or Italian sausage (mild or hot) removed from the casing. If using the plain ground pork, be generous with the salt and pepper and feel free to add a few additional seasonings like fennel, onion powder, garlic powder and/or paprika. Sausage comes with the seasonings already mixed in so it’s got a lot more flavor straight out of the gate.

Leeks – these are a great (slightly milder) fall alternative to onions. Make sure to wash them well as dirt likes to hide in the center. You can substitute a small yellow onion if you don’t have leeks on hand.

Fennel – even if you’re not a fan of raw fennel, I encourage you to try it cooked. The intensity of its signature licorice flavor mellows out quite a bit when cooked. It’s also a great digestive aid!

Apples – a medium chopped apple brings a touch of tart sweetness (I like using a sweet/tart variety like Honeycrisp) to the savory elements of the stuffing.

Cranberries – use fresh or frozen whole cranberries for a pop of color and brightness to the stuffing. They complement the pork/sausage and apples so well!

Sage – what would a fall stuffing be without some sage? This is a great fall herb to bring all the flavors together. Rosemary would be a good alternative if you prefer.

Stuffing the roasted delicata squash "boats" with the ground pork filling.

HOW TO MAKE THE STUFFING

While the delicata halves roast in the oven getting all nicely caramelized and fork tender, the stuffing is easily made in a skillet on the stove-top.

To a large pan, add olive oil and the pork (or sausage). Cook over high heat until browned, breaking it up into small pieces with a spatula as it cooks.

Once browned, add the leeks, fennel and apples to the skillet. Stir everything together and cook for about 5 minutes until starting to soften.

Next, add the cranberries and sage. Toss to combine and cook for 1-2 minutes until the cranberries are just warmed through.

Season the stuffing with salt and pepper to taste then spoon into the roasted delicata squash to serve.

Stuffed delicata squash on a plate bursting with fall ingredients of ground pork, cranberries, fennel and leeks.

SUBSTITUTIONS FOR STUFFED DELICATA SQUASH

  • Use another protein – ground turkey, beef or even crumbled tempeh would all work well in this recipe.
  • Swap pears for apples – while you’ll lose the crispy texture of the apple, pears are another great fall fruit option that go well with the flavors of this stuffing.
  • Try another type of squash – I maintain that delicata squash is one of the best for stuffing but, honeynut (not butternut!) or buttercup squash are both similar tasting and have edible skin like delicata making them a good choice as well. Kabocha is another option but you’ll likely have to roast that longer than the other varieties based on its larger size.

Stuffed delicata squash boats are an easy gluten-free fall dinner packed with flavors everyone will love.

These stuffed delicata halves are reminiscent of my Sausage Cranberry Apple Stuffing Muffins.

The two recipes have a similar ingredient list and flavor profile and they both make delicious additions to a Thanksgiving spread.

While the stuffing muffins are a great stand-in for traditional stuffing, these stuffed delicata squash make an easy, non-traditional option for the turkey itself!

They’re especially great for a small Thanksgiving crowd. Or, if in this crazy year of 2020, you’re spending the holiday with just your own family.

Just swap in ground turkey for the pork and boom – you’ve got your turkey dish covered!

With all the time you saved not roasting an actual turkey, you can focus more on the sides – the best part anyway!

Roasted stuffed delicata squash bursting with savory and sweet fall flavors that complement the tender, slightly sweet squash perfectly.

If you’re just serving them as a weeknight dinner, pair with a simple salad like this baby kale salad (I’d probably leave off the chickpeas) and enjoy an easy seasonal meal!

I hope you snag some delicata squash while they’re around (they don’t stick around as long as some other squash staples like acorn, butternut and spaghetti!) and give this recipe a try!

More squash recipes to enjoy this time of year:

Twice Baked Kale and Pecorino Acorn Squash

Butternut Squash Pita Nachos

Kabocha Squash Chili

Creamy Pesto Spaghetti Squash Noodles

Wild Mushroom Couscous Lamb Stuffed Kabocha Squash

Stuffed Delicata Squash

Stuffed Delicata Squash

Yield: 4 servings
Prep Time: 15 minutes
Cook Time: 30 minutes
Total Time: 45 minutes

Roasted delicata squash is stuffed with a simple ground pork, apple and cranberry mixture for a vibrant and delicious fall flavored meal!

Ingredients

  • 2 large delicata squash, cut in half lengthwise, seeds removed
  • 2 tablespoons extra virgin olive oil, divided
  • salt and pepper to taste
  • 8 ounces ground pork or Italian sausage removed from casing (*see note)
  • 1 small leek, thinly sliced and thoroughly washed
  • 1 small fennel bulb, thinly sliced
  • 1 medium apple, chopped (use a sweet/tart variety like Honeycrisp or Gala)
  • 1/2 cup fresh or frozen cranberries
  • 3 leaves fresh sage, minced

Instructions

  1. Preheat oven to 375°F.
  2. Rub 1 tablespoon of the olive oil over the cut side of each squash half and season with salt and pepper. Place cut side down on a lightly greased baking sheet. Roast for 25-30 minutes until the squash is fork tender and starting to caramelize/turn golden brown around the edges.
  3. While squash roasts, place a large skillet over medium-high heat.
  4. Add the remaining tablespoon of olive oil to the pan along with the ground pork and cook until browned, breaking up with a spatula as it cooks.
  5. Once browned, add the leeks, fennel and apple to the pan. Reduce the heat to medium, stir to combine and cook until slightly softened, about 5 minutes.
  6. Add the cranberries and fresh sage, cook until cranberries are just heated through, about 2 minutes.
  7. Season to taste with salt and pepper.
  8. Spoon the filling into each roasted squash half and serve.

Notes

*If using Italian sausage, make sure to remove the casing from each sausage link so the sausage crumbles as it cooks. Feel free to use either milk or hot sausage depending on preference.

Nutrition Information:
Yield: 4 Serving Size: 1
Amount Per Serving: Calories: 383Total Fat: 24gSaturated Fat: 7gTrans Fat: 0gUnsaturated Fat: 16gCholesterol: 64mgSodium: 271mgCarbohydrates: 23gFiber: 6gSugar: 11gProtein: 20g

This website provides approximate nutrition information for convenience and as a courtesy only. Nutrition information can vary for a variety of reasons. For the most precise nutritional data use your preferred nutrition calculator based on the actual ingredients you used in the recipe.

DID YOU MAKE THIS RECIPE?

Please leave a comment & rating below or share a photo on Instagram and tag @runningtothekitchen

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Sonal

Thursday 8th of October 2020

Wow that looks super festive. I bet it tasted amazing. Bookmarking it.

Alisa Infanti

Thursday 8th of October 2020

The fennell added such a nice unexpected flavour to this delicious recipe.

Beth

Thursday 8th of October 2020

This looks so delicious and tasty! I can't wait to give this recipe a try!

Jen

Thursday 8th of October 2020

Love that you added cranberries to this! Gives it a fun burst of flavor but also a pop of color. I'm so jealous you had these squash growing in your garden. We finally moved into a house that I can make some space for one this year.

Jess

Thursday 8th of October 2020

This dish screams Fall!

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