Winter Squash Enchiladas

This is an old dish that I made for brunch the other day and remembered how awesome it is. You can go all out and make your own sauce and tortillas (homemade tortillas are so delicious, and a great kitchen-zen moment too), but these enchiladas will taste great with premade tortillas and a good can of green enchilada or a chile verde sauce. A lot of the flavor comes from the sauce used, so look for something that has a tangy kick to it and peppers high up in the ingredients list. The original recipe used sauteed kale, but this time I diced up half a dozen Red Bull brussel sprouts and a few Rainbow Lacinato kale leaves (stems and all) and steamed them from 5 minutes. The diced brussel’s added a lot of flavor and texture to the finished dish, and the smaller squashes that we got from Danny are the perfect size to make 20 enchiladas (which served 10 people when I paired them with 10 scrambled eggs and 3 cut up apples and oranges on the side). Total prep time was just under an hour.
One last word about the sauce, you should look for a great tomatillo sauce recipe in the summer months, they are so easy to grow and have a very good consistency when roasted and blended with peppers and onions. It’s also a sauce that preserves or freezes really well. I have a dozen jars and look forward all summer and fall to using it with these winter enchiladas. If Danny ever decides to grow them for the share, I’ll definitely send in the recipe.


1 large grapefruit-sized winter squash (I used the Little Cutie squash this time)
2 cups chopped winter greens of choice (kale and brussel sprouts were used here, but chicories, cabbage, turnip greens, etc. would also work great)
20 4-6 inch corn tortillas
2 cups green enchilada sauce (tomatillo sauce was used here, but chile verde sauce also works)
2 cups grated cheddar cheese (a little Monterrey Jack mixed in is good too)
2 teaspoons Cumin
2 teaspoons Coriander
salt to taste


Preheat oven to 400.

With a large knife cut the squash in half, and scoop out the seeds and stringy innards. Stab the skin of each half a few times to create ventilation while roasting. Pour about a tablespoon of olive oil into a pan and spread it out with the flat side of each squash. Place the squash flat side down in the pan and bake for 35-40 minutes, until the flesh is easily pierced with a fork.

While the squash is baking, warm a ungreased griddle or cast iron pan, and heat up 20 tortillas, cooking each side for 30 seconds. This will make the tortillas more pliable and easy to roll up. If you are making your own tortillas, once you’ve pressed the masa into shape you just need to par cook each side until it holds together, they will finish cooking in the oven. Keep the warmed tortillas folded up in a few dish towels on top of the stove to keep them warm.

Preparing the greens: Wash the greens and shake off the excess water. If you are using brussel sprouts (which I strongly recommend) hold each one in your non-cutting hand and dice it into small strips with a sharp knife. You can keep the tougher stem piece on and chop that up as well. Dice your kale, collards or other greens to a similar size as the brussels. Heat ½ inch of water in a covered pot and using a steamer or colander steam the greens for 5 minutes. When finished set to one side.

When the squash is done, let it sit face up on the counter for 5 minutes to cool enough to touch, but leave the oven on as you will be baking the enchiladas soon.  Using a spoon scrape out the squash flesh and put it in a medium sized bowl. Add the steamed greens, cumin, coriander and salt. Mix until well incorporated.

Building the enchiladas:  You can use either two 5×9 inch casserole pans or one 9×13 inch pan.  Pour ¼ cup of the enchilada sauce in the pan and spread it out. Take a tortilla in your hand and spread one large spoonful of squash mixture into it. Sprinkle in 1 tablespoons worth of cheese, roll it up, and place it in the pan. Repeat this with the rest of the tortillas, until the pan is full. The tortillas may start to unroll but as you fill the pan they will be pushed together.  When you have finished with all the tortillas, pour the remaining amount of sauce over them and spread it out so that all the tortillas are at least partially covered. Cover the enchiladas with the remaining cheese, cover the pan with tin foil and bake for 30 minutes, uncovering for the last 10 minutes to brown the cheese.

Remove and serve immediately.

| December 30th, 2012 | Posted in Brussel Sprouts, Recipes, Winter Squash |

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