Winter Squash Enchiladas

by Nov 30, 2016

Jumbled together in bins at the market, you’ll find all kinds of winter squash: Delicata, Butternut, Red Kuri, Kabocha, Acorn, Buttercup, a variety of pumpkins. Pick one or two and bring them home, they improve with age, and will happily rest on your counter for weeks. Most are interchangeable in cooking, with subtle differences in flavor and moisture content. (Spaghetti squash is the exception.  A unique veggie, that one. I think they should be sold separately. But I digress…)


With regular (i.e. non-spaghetti) winter squash, I go small, as they are easier to deal with avec knife.  Just imagine:  you’ve got to be able to cut it in half, scoop out the seeds, and chop away the outer peel (not necessary with Delicata and Acorn).  From there, what you do depends on what you’re cooking.  May I suggest bite-size chunks and these fantastic enchiladas?


Winter Squash Enchiladas

serves 8–10; adapted from "Three Sisters Winter Squash Enchiladas" by Cara Jenkins, in Farm-Fresh and Fast, a cookbook created by the CSA Coalition of Madison Wisconsin


Enchilada Sauce

  • 4 tbsp unsalted butter
  • 2 cloves garlic, minced
  • 3 chipotle in adobo (½ 7-ounce can with some sauce) or 3 tablespoons chile powder
  • ½ cup all-purpose flour
  • 2 cups tomato passata or tomato sauce Mutti
  • 2 cups vegetable broth made with 1 cube Edward & Sons or Rapunzel bouillon and 2 cups water


  • 2 tbsp olive oil
  • 2 cloves garlic, minced
  • 1 teaspoon ground cumin
  • ½ teaspoon dried oregano
  • 1 small winter squash, halved, seeded, peeled, and chopped into ½-inch dice about 2 pounds yielding about 3 cups chopped
  • 1 15-ounce can black beans, drained and rinsed
  • 1 15-ounce can chopped tomatoes
  • 1 4-ounce can diced green chiles
  • ½ cup frozen corn kernels
  • 4 tbsp cream cheese cut into tablespoon-sized chunks
  • a few pinches of Kosher salt and several grinds of black pepper


  • 1 tbsp unsalted butter
  • 10 6-inch flour tortillas
  • 2 cups cheddar cheese, shredded

For serving: sour cream, chopped cilantro leaves,and lime wedges



  1. Heat butter in medium sized saucepan over medium-high heat. Add the garlic and sautée until fragrant, about 30 seconds. Add chiles (or chile powder) and stir to combine. Sprinkle the flour into the saucepan, stir and cook for a couple minutes (you're making a roux!) Whisk in the tomato sauce and broth, and cook, stirring frequently, until thickened and bubbly, about 3–4 minutes. Lower heat and let gently simmer while you proceed with the next steps.


  1. Heat olive oil in large frying pan over medium-high heat. Add the garlic and sautée until fragrant, about 30 seconds. Add the cumin and oregano and cook for 30 seconds. Add the squash and cook for 10–15 minutes, until almost soft. Add the black beans, tomatoes, green chiles, and corn, and cook for about 5 minutes. Reduce heat to low and add the cream cheese, stir to combine. Taste and sprinkle in a couple pinches of salt and several grinds of black pepper. Remove from heat.


  1. Preheat oven to 350° F. Butter a 13x9 inch glass pyrex baking dish, or something similar, and set aside.

    Lay out the tortillas on your work surface and divide the filling between them (approximately 1/2 cup filling for each), then divide 1 cup of the cheese between them. Roll up each tortilla and place seam side down in the prepared baking dish.

  2. When all are rolled and in the baking dish, pour the enchilada sauce over the top. Sprinkle with remaining 1 cup cheese. Set baking dish on a rimmed sheet pan to catch any drips and bake for 30 minutes on middle rack of oven, until hot throughout and cheese is browned on top. Serve with sour cream, chopped cilantro leaves, and lime wedges.


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