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+ servings
Roasted Winter Squash Enchiladas
Smoky delicious roasted winter squash enchiladas topped with a bright cilantro and arugula salad.
Recipe Type: Dinner
Makes: 6 servings
Author: Brooklyn Supper
For the Roasted Squash
  • 1 medium or 2 small red kabocha or butternut squash peeled and seeded
  • 2 tablespoons grapeseed oil (or other heat tolerant neutral cooking oil such as canola)
  • 1/2 teaspoon chipotle chili powder
  • 1/2 teaspoon sea salt
For the Enchilada Sauce
  • 2 tablespoons grapeseed oil, divided
  • 1/2 red onion, minced (reserve other half for salad)
  • 1/2 teaspoon sea salt
  • 2 cloves garlic, smashed, peeled, and minced
  • 1 28- ounce can Muir Glen Organic Fire Roasted Crushed Tomatoes
  • 1 - 3 in canned chipotle peppers adobo sauce plus 2 tablespoons sauce
  • 1 cup vegetable or chicken broth
  • 1 teaspoon ground cumin (fresh ground if possible)
For the Filling
  • 1 can pinto beans drained and rinsed
  • sea salt
  • 12 corn tortillas
  • 8 ounces grated Monterrey Jack cheese
For the Salad, adapted from Sprouted Kitchen
  • 1/2 red onion sliced, reserved from enchilada sauce
  • juice of 1 lime
  • sea salt
  • 1 bunch cilantro stems removed and chopped
  • 2 handfuls arugula chopped
  • 1 avocado cubed
  1. Preheat oven to 425 degrees F.
  2. Toss cubed squash with oil, chili powder, and sea salt. Spread out on a rimmed baking sheet. Roast 40 - 45 minutes or until squash is golden with crisp edges; use a spatula to flip squash halfway through cook time. Set squash aside to cool. Set oven heat to 350 degrees.
  3. Meanwhile, make the sauce. Set a large, deep-sided skillet or Dutch oven over medium heat, add 1 tablespoon grapeseed oil, and then the onion and sea salt. Cook until onion is translucent and soft, about 5 minutes. Add garlic and sauté 1 minute more. Spoon onion mixture, canned tomatoes, 1 chipotle pepper, adobo sauce, broth, and cumin into a blender pitcher and puree. Taste and add sea salt or 1 -2 additional chipotle peppers to taste; puree once more if needed.
  4. Set the same skillet used for onions over medium heat, add remaining tablespoon oil, and then pour in the enchilada sauce. Cook sauce, stirring often, 15 minutes.
  5. While sauce cooks, warm beans in a small saucepan. Add sea salt to taste and several tablespoons enchilada sauce. Wrap corn tortillas in a foil packet and warm in the oven 5 - 10 minutes.
  6. Grease a 9 x 13-inch baking dish. Add several tablespoons enchilada sauce to the bottom.
  7. To assemble enchiladas, dip corn tortilla in enchilada sauce, then lay flat and add 1 - 2 tablespoons each cheese, squash, and pinto beans. Carefully roll and set in baking dish seam side down. Repeat for all remaining tortillas, squishing the rolled ones together to make room. Top rolled tortillas with remaining enchilada sauce and cheese. Slide into oven and bake 15 minutes, or until cheese has melted and sauce is bubbling.
  8. To make salad, toss red onions with lime juice and sea salt in a large bowl. Just before serving, add cilantro, arugula, avocado, and sea salt to taste.
  9. To serve, use 2 spatulas to set 2 enchiladas on each plate and top with a handful of salad.