Chili Roasted Winter Squash

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We grow a pretty big garden, each year without fail, we include at least a couple kinds of winter squash. Now, the thing about winter squash is that it tends to be rather prolific. If it is happy where it is growing, you are going to end up with a lot of squash for your efforts – like the 150 or so we ended up with this year. Crazy, huh? But, I don’t mind a bit, because it is such a useful and versatile ingredient. And, if you do have to buy it, it’s usually very inexpensive, especially in the months right around the holidays – a big plus in my book.

When my husband’s family gets together for Thanksgiving and Christmas, the cooking never falls to just one person – everyone brings along a few favorite dishes to share. There is never a question about what they want me to bring, though – it is this Chili Roasted Winter Squash, every time! It is sweet and spicy and rich and comforting. And very easy to prepare – you can even make it ahead and reheat it right before the meal.


Combine everything well – I just use my fingers to kind of squish it all together, because the brown sugar is a bit of a pain to get mixed in any other way. [a note about the chile powders – I like to combine them to get a better depth of flavor, and to vary the heat a bit, depending on who I am feeding. If I had to use just one, it would probably be the Chimayo, which has a medium heat.]

When the squash is very soft, with lots of nice caramelization on it, dot with 2 tablespoons butter, cut in small pieces, and sprinkle the seasoning mix over the cubes. [You might not use it all, but if that happens to me, I just put it in an empty spice jar to use next time, or maybe to sprinkle on a roasting chicken, or some pork chops I am throwing on the grill.]
Return to oven for another 5 minutes, stir around a bit, and roast for another 3 or 4 minutes. The spice rub can burn if you leave it in there for too long, so keep an eye on it.

Serve hot – this goes really well with pork, or chicken, alongside a big bowl of black beans and rice. It is actually quite good just warm, or at room temperature as well, which makes it a perfect choice for pot luck dinners. And trust me – it’s sure to wake up your Thanksgiving dinner!



In a small bowl, combine:




Butternut squash works well for this, because it is easy to peel and cut into cubes. Discard the seeds, or roast them like pumpkin seeds, if you like.

Line a sheet pan with parchment paper, and preheat the oven to 425º, with the prepared sheet pan inside. Preheating the pan gets things going more quickly. Peel a medium sized butternut squash, and cut into 1 inch cubes. Place in a roomy mixing bowl. Drizzle a few tablespoons of olive oil over the squash, and stir with a wooden spoon to coat cubes evenly. Carefully remove the hot sheet pan from the oven, and spread out the squash cubes evenly on it. Season with generous pinches of kosher salt, and some grinds of black pepper.

Place the pan back in the oven, and roast for about 25 minutes. The squash should be getting softer by this time, and start to get a little color on it. Use tongs or a flat turner to turn all of the cubes over so that they will brown on the other side. Return to the oven for another 5 to 10 minutes.

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