Stuffed Winter Squash & Winter Break

Coming at ya with a quick little post/update and a recipe for Stuffed Winter Squash. We’re packing some hearty roasted winter squash with spicy sausage, apples, kale, and aged cheddar. A cozy recipe on repeat for the cold days ahead.

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Winter Break

Has this fall been as crazy for you as it has for me? You may have noticed that I have taken a small break from this space. Things have just been wild around here! My professional life has been more demanding, and of course the whirlwind of the holidays. Matt and I are also working on some really big projects for next year. These projects will have an implication for this little place, but I hope you’ll find it as exciting as we do. 

I’ll be announcing in the New Year, but do know we are working our little tails off behind the scenes. For that reason, this will be the last recipe of the year, but I do have a little garden giveaway for the holiday season in the works. If you’re a regular reader, I appreciate you more than you know 🙂 I hope you can hang with us through this break. OK, onto the recipe!

Stuffed Winter Squash

A few quick notes on this recipe. First let’s talk squash. The size of your squash will determine how long you bake before stuffing. If you go with small winter squash, like mini pumpkins, you’re looking at 20-30 minutes. If you go with medium squash, like small acorns or red kuri, you’re looking 35-45 minutes.

Next let’s talk stuffing. I love to use a good aged cheddar, because it pairs really well with the apples. Don’t be scared of the amount of kale, as it cooks down significantly. I prefer a firm, tart apple like pink lady for this particular recipe. Finally, use spicy sausage if you can handle the heat! 

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Stuffed Winter Squash

Hearty winter squash stuffed with spicy sausage, apples, kale, and aged cheddar. A cozy recipe on repeat for the cold days ahead.

Prep Time15 mins

Cook Time1 hr

Total Time1 hr 15 mins

Course: Main Course

Cuisine: American

Keyword: fall, healthy

Ingredients

• 6 small or 3 medium winter squash
• 2 T olive oil divided
• S&P
• 2 shallots chopped
• 1.5 lbs spicy pork sausage
• 1-2 apples diced
• 4 cups kale washed and torn into bite-size pieces
• 2 tablespoons heavy whipping cream
• 1.5 cups aged cheddar cheese

Instructions

• Preheat oven to 400 F. If using small squash, cut the tops off. If using medium squash, cut in half. Scoop out seeds. Brush with 1 tablespoon olive oil and season with salt and pepper. Place on baking sheet and roast for 20-45 minutes depending on size (20-30 for small; 35-45 for medium). Remove once tender and set aside until stuffing is ready.
• Meanwhile, heat remaining 1 tablespoon olive oil in large nonstick skillet over medium heat. Add shallots and saute 2-3 minutes. Add sausage, breaking up with a wooden spoon, and cook until just browned (if there is a significant amount of fat in the pan, you could drain at this time). Add apples and kale, stirring until kale has significantly cooked down. Add cream and cheddar cheese, stirring to combine.
• Once squash is fork tender, scoop stuffing into squash. Return to oven for 10-15 or until heated through. Enjoy!

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