Chili Roasted Butternut Squash

This is a rewind post, brought up to the top of the blog because of reader popularity. If you haven’t seen it before, I hope you enjoy it today! Time for another piece of the puzzle – the Thanksgiving Dinner puzzle!

How does your family “do” Thanksgiving? Do you have the same treasured old stand-bys year after year, or do you like to find the latest trends? Does one person do all the cooking, or do you split things up, with different people bringing things to share? Do you travel? Stay home and have company over?

I’m pretty nosy aren’t I? Seriously, I do love hearing about the traditions in other families, so if you would like to answer any of these burning questions that I have posed, please feel free to do so down in the comments.

I’ll even answer my own questions: We use a mixture of old and new recipes, we split up the cooking, and we always go to my sister and bother-in-law’s in Massachusetts. There’s poker, wine, Black Friday shopping and a lot of thankfulness that we get to be together.

What there is mostly though, is food. Growing up in a family of great cooks means you have to be on your toes when it comes to the holidays, because the expectations are high. I’ve already told you about our favorite Southwest Cornbread Dressing, and today, I have another side dish that may be out of the ordinary. It’s Chili Roasted Butternut Squash and it truly is one of the best ideas I have ever had.

I’m not sure I would allowed in the door if we showed up at Larry’s family’s Christmas dinner without a huge dish of this stuff, and we enjoy it just as much at Thanksgiving time. It is really easy too, which is nice when you have a lot of other things to prepare – you can even do it ahead and reheat it at dinnertime if you’d like.

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Chili Roasted Butternut Squash

Any kind of large, smoother skinned winter squash will be great in this recipe.

Author: Donalyn Ketchum

Recipe type: Vegetables, Side Dish

Serves: 8 - 10 servings

Prep time: 15 mins

Cook time: 70 mins

Total time: 1 hour 25 mins

Ingredients

Butternut squash - about a 4 to 5 pounder
2 tablespoons olive oil
kosher salt & fresh cracked pepper
¼ cup light brown sugar
1 &1/2 teaspoons ground cumin
1 &1/2 teaspoons smoked paprika
1 teaspoon chipotle chili powder
1 teaspoon granulated onion powder
½ teaspoon ground cinnamon
½ teaspoon granulated garlic powder
2 tablespoons butter
additional salt & pepper to taste

Instructions

Set the oven to 350º. Line 2 heavy baking sheets with parchment paper. It's best to use two baking sheets, to ensure even roasting and to get some nice color on the squash.
Begin preparing the squash by cutting it in half from top to bottom.
Lay the halves cut side down on a cutting board. [it is best to put on a pair of disposable gloves when cutting up squash - the moisture in winter squash turns into an impenetrable coating on your hands once it dries. Not harmful, but no fun to get off either, so save some time and put on the gloves]
Use a vegetable peeler to peel all of the skin from the outside of the squash.
Flip the halves over, and scoop out the seeds.
Cut the squash into 1 inch cubes.
Place all of the cubes in a large bowl, and drizzle over the oil oil. Sprinkle on the salt and pepper, and mix with a large spoon, to get everything coated in the oil.
Spread the squash out on the prepared baking sheets - it should be in a single layer as much as possible.
Roast the squash in the oven for 50 to 70 minutes, stirring every so often to get it evenly cooked.
Meanwhile, in a small bowl, combine the brown sugar, cumin, paprika chili powder, onion powder, cinnamon and garlic powder. If needed push the mixture through a mesh strainer to get out any lumps.
When the squash is easily pierced with the tip of a sharp knife, and it pretty soft, dump all of the squash onto one baking sheet. Melt the butter and pour over the squash, followed by the sugar and spice mixture. Gently mix it all together, and then spread it out evenly again [though it will be more crowded now of course]
Return to the oven for another 10 minutes or so, until the sugar has somewhat caramelized.
Remove to a bowl and serve hot. If making ahead, allow it to cool still on the sheet pan, then refrigerate until dinner time. It will take 30 minutes or so to reheat, in a casserole dish, uncovered at 350º.