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Roasted Delicata Squash Stuffed with Kale and Maple Cinnamon Roasted Mushrooms {paleo + vegan option}

  • Author: Nyssa Tanner
  • Total Time: 1 hour
  • Yield: about 6 servings 1x


Roasted delicata squash stuffed with kale and maple cinnamon roasted mushrooms is literally bursting with brilliant seasonal flavor and color!


  • 3 delicata squash, halved and de-seeded
  • 1 1/2 tablespoons ghee, avocado or coconut oil 
  • 1 teaspoon sea salt 
  • 1/2 pound of bacon, cut into thin strips crossways (optional – see notes)
  • 2 pounds of assorted mushrooms, trimmed and sliced/diced if large
  • 1/2 teaspoon cinnamon 
  • 1/4 teaspoon salt 
  • few grinds of black pepper
  • 1 tablespoon maple syrup 
  • 1 bunch of kale, washed and cut into small bite size pieces
  • 2 cloves of garlic, chopped 
  • 1/4 cup broth + more as needed
  • salt and pepper to taste 
  • olive oil for finishing
  • flaky sea salt 
  • 1/2 cup toasted walnuts (see notes for toasting suggestions)
  • 1/2 cup pomegranate arils 


  1. Preheat oven to 425F. 
  2. Melt and drizzle ghee or coconut oil over squash halves, sprinkle with sea salt and use your hands to thoroughly coat the whole squash (skin side, too!). 
  3. Bake, flesh side down for 30 minutes, until starting to brown and soften. 
  4. Very carefully flip squash and bake another 15 minutes, to release some of the moisture and caramelize a little more. 
  5. While squash is cooking prepare the filling. 
  6. Cook bacon in a large skillet over medium heat until crisp. 
  7. Move to a paper towel lined plate and pour off all but about 2 tablespoons bacon fat. If not using bacon, heat 2 tablespoons of cooking oil of choice over medium heat to skillet before the next step. 
  8. Add mushrooms and fry over medium heat until soft and caramelized. About 14-16 minutes (this will vary depending on the size of the mushrooms. You don’t want to skimp out on this step – the darker and more caramelized the mushrooms the better the flavor!) If the pan starts getting too dry and mushrooms are sticking to the bottom of the pan before they’re all the way cooked, add a splash of broth every so often to loosen things up. Once mushrooms are tender and caramelized, add cinnamon, 1/4 teaspoon of salt, black pepper and maple syrup and cook another 2 minutes – stirring frequently. Move to plate with bacon. 
  9. Add 1/4 cup broth to the skillet with garlic and kale and cook, scraping up any brown bits from the bottom of the pan, until  kale is wilted and tender, about 6-8 minutes. Again you can add a splash of broth here or there if pan is dry before kale is cooked. Season kale with about 1/2 teaspoon of salt. 
  10. Add mushrooms and bacon back to the skillet and stir together to combine. Taste and season with salt and pepper, cooking for a few more minutes to marry flavors. 
  11. Divide filling evenly into cooked squash halves, and move back into the oven for a few minutes to warm through.
  12. Finish with a drizzle of olive oil and flaky sea salt, and top with toasted walnuts and pomegranate. 


  • For a vegetarian version skip frying the bacon and add 2 tablespoons of your fat of choice to the skillet before starting to fry mushrooms. 
  • While oven is still hot you can toast your walnuts. Usually about 3-4 minutes will do it at this temperature. Watch them carefully because they burn easily. 
  • Squash can be roasted ahead of time, and filling can be made in advance as well. 

  • Prep Time: 15 minutes
  • Cook Time: 45 minutes