Delicata Squash with Caramelized Onion, Beef & Bacon Stuffing {Paleo, Whole30}

Delicata squash is roasted to perfection and stuffed with ground beef, caramelized onions, bacon, spinach, mushrooms and seasonings.  This cozy paleo and Whole30 stuffed squash is great for any meal or as a side dish.   Savory, filling and healthy!

I’m still on a huge winter squash kick and I’ve decided, wholeheartedly, that my favorite way to enjoy winter squash is roasted and stuffed with ALL the goodies.

And by goodies, I’m of course referring to Paleo and Whole30 compliant goodies like sugar-free bacon, grass fed ground beef, and caramelized onions.  Throw a few more veggies in there and you have everything you’ll ever need for your Whole30 and beyond, in my opinion 🙂

Even though the stuffing for this delicata squash is by all means savory, there’s actually a good amount of naturally delicious sweetness here too, since we’re roasting the squash to bring out all the yummy caramel flavor AND caramelizing our onions!  Can we all take a moment to appreciate the chemical reaction known as caramelization?!   Science is just brilliant 🙂

Between the onions, squash, beef, bacon, mushrooms and spinach, you are set for life – just you wait and see.  As for the bacon – If you need the recipe to be Whole30 compliant I highly recommend trying out the sugar free pork bacon from U.S. Wellness Meats.

It’s been my favorite for years – ever since my first Whole30.  I like to buy a ton of it, keep it in the freezer and then just thaw it as needed.  It’s thick, cooks up super crispy without burning, and, contains just pork and salt.  Hallelujah for Whole30 complaint bacon!   (Just a hint – I love using the rendered bacon fat to caramelize the onions and cook the rest of the stuffing.  You don’t NEED to do this, but it definitely adds more of that great bacon flavor to the final result.)

Overall this recipe is super straightforward, although there are several different steps.  In summary, you cook the bacon first – especially if you want to use the rendered fat for the rest of your cooking.  Then you simultaneously roast the squash, while two separate skillets are sizzling on the stovetop – one for caramelizing the onions, and the other for cooking the veggies and beef.

The beauty of it all is that everything is ready at the same time – multitasking in cooking makes me happy!  Lastly, you just stuff the squash and broil for a few minutes to get everything perfectly toasty.

Since it does take a solid 40 minutes from start to finish, it’s also a great recipe to make ahead of time, (leftovers are great reheated in the oven) or even to prep/cook parts of it ahead of time so you can put it together really quickly on a weeknight.  I hope you’re ready to get started!  I know you’re going to love this one – get that oven preheated and let’s cook!

Delicata Squash with Caramelized Onion, Beef & Bacon Stuffing {Paleo, Whole30}

Delicata Squash with Caramelized Onion, Beef & Bacon Stuffing {Paleo, Whole30}

Delicata squash is roasted to perfection and stuffed with ground beef, caramelized onions, bacon, spinach, mushrooms and seasonings.  This cozy paleo and Whole30 stuffed squash is great for any meal or as a side dish.   Savory, filling and healthy!

Author: Michele Rosen

Prep Time: 10 minutes

Cook Time: 30 minutes

Total Time: 40 minutes

Course: Anytime

Cuisine: Paleo, Whole30

Servings: 6

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4.64 from 25 votes

Ingredients

• 3-4 delicata squash Depending on their size
• 1 tsp cooking fat and sea salt for roasting
• 1 lb grass fed ground beef
• 6 slices nitrate free bacon cut into pieces
• 1 large onion sliced thin
• 3 tbsp bacon fat or ghee, or coconut oil for caramelizing
• 1/2 tsp sea salt for caramelizing onions
• 1 cup mushrooms chopped
• 2 cloves garlic minced
• 2 handfuls baby spinach chopped
• 2 tsp organic poultry seasoning
• 3/4-1 tsp salt or to taste
• 1/8-1/4 tsp black pepper or to taste

Instructions

Roast the Squash:

1. Preheat your oven to 425 degrees and line a large baking sheet with aluminum foil.
2. Cut each squash in half lengthwise and scoop out all the seeds and strings, forming a “bowl” for the stuffing in the center.

3. Brush each squash half with cooking fat and sprinkle lightly with sea salt. Place face down on foil lined baking sheet, and roast in the preheated oven for about 20-30 minutes, or until the back of the squash feels soft when pressed gently. Cooking time will vary depending on the size of your squash. Once done, remove from oven, leave the squash halves on the baking sheet and set aside until ready to stuff.

Make the Stuffing:

1. Meanwhile, heat a large heavy skillet over med/hi heat to cook the bacon. Add bacon pieces and stir to evenly brown, once crisp, remove with slotted spoon to drain on paper towel, set aside. Reserve rendered bacon fat if planning to use, or discard if using another cooking fat.

2. To caramelize the onions, you can either use 3 Tbsp of rendered bacon fat, or a preferred cooking fat. You can use the same skillet you cooked the bacon in, or a separate one, since the onions will cook separately from the rest of the stuffing.

3. Heat cooking fat in skillet over low heat and add all the sliced onions, stirring to coat. Sprinkle with 1/4 tsp salt and cook over low heat, stirring every 5 minutes to prevent burning. Once onions have been cooking for about 20 minutes and are deep golden brown, remove from heat and set aside.

4. Meanwhile, while the onions are caramelizing, add a bit of reserved bacon fat or cooking fat to a separate large skillet and heat over medium.  Add chopped mushrooms and stir, cook for a minute until soft, then add garlic. Continue to cook and stir until garlic softens, then crumble in the ground beef. Sprinkle with 3/4 tsp salt, the pepper and poultry seasoning, and cook, stirring to break up lumps and evenly brown.

5. Once beef is browned, lower heat and stir in spinach to wilt. Remove from heat and add in the caramelized onions with a slotted spoon, leaving excess grease in the skillet.  Stir in the cooked bacon to complete the stuffing.

Stuff and broil:

1. Preheat your broiler and generously fill all roasted squash halves (stuffing should fill 6-8 squash halves depending on size) then place the baking sheet under broiler and broil until the top is nicely “crisp”, abut 2-5 minutes. Remove and garnish with fresh parsley if desired. Enjoy!

Recipe Notes

*Nutrition is calculated using a value of 6 servings, or about 1/2 squash per serving.  Serving size will vary depending on whether you serve as a meal or side dish - I calculated these servings as meal portions.

Nutrition

Calories: 369kcal

Carbohydrates: 13g

Protein: 18g

Fat: 27g

Saturated Fat: 10g

Cholesterol: 72mg

Sodium: 704mg

Potassium: 755mg

Fiber: 2g

Sugar: 3g

Vitamin A: 2490IU

Vitamin C: 18.9mg

Calcium: 61mg

Iron: 2.6mg

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What I Used to Make My Stuffed Delicata Squash:

Want More Paleo and Whole30 Winter Squash Recipes?  Try One of These!

Caramelized Onion, Sausage, Apple Stuffed Acorn Squash

Roasted Acorn Squash with Sausage Apple Cranberry Stuffing

Roasted Butternut Squash Hash with Bacon and Apples

Easy Pumpkin Chili

Creamy Tomato Basil Chicken with Roasted Butternut 

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