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

Loves! Hello! This is the one last little recipe I want to get out to you before the day of gratitude and feasting begins, and it is a GOOD one. This is a recipe for all my side dish lovers out there. The one’s who are into the vibrant colors of the season, and all the delicious flavors that exist on the other side of a hot oven. I see you and I’m here for you today with this recipe for roasted delicata squash stuffed with kale and maple cinnamon roasted mushrooms!

YESSSS.

Roasted delicata squash stuffed with kale and maple cinnamon roasted mushrooms is literally bursting with brilliant seasonal flavor and color!
 
I know we’re a bit last minute with the whole turkey day menu conversation (ahem), but I’m betting there’s a least a few of you out there reading this still searching for that most delicious side dish to bring to the table.

Or maybe you’re reading this after the whole turkey day thing, and just looking for a crazy delicious stuffed squash recipe.

Either way, you’re in luck. Because this one, piled high with tender sautéed kale, maple cinnamon roasted mushrooms (YES!!), bacon (if that’s your thing), and topped with bright and sweet pomegranate seeds and toasty walnuts in all it’s colorful brilliance, is begging you to choose it!

If you listen closely, you might even hear the words…

(pick me! pick me!)

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


 

what’s to love about this pretty stuffed squash?

 
It travels well, is PACKED with nutrients (you know, to make up for the fact that you’re going to try a slice of each kind of pie 😝) and is literally bursting with seasonal flavor.

I’m not sure there could be a more nutrient powerhouse combo than:

  • delicata squash – Vitamin A + Vitamin C + Potassium + so much more vitamin and mineral diversity
  • mushrooms – high in anti-oxidants and rich in anti-inflammatory properties, these flavorful little gems host a variety of B vitamins, and moderate amounts of Copper, Selenium, Potassium and Phosphorus
  • kale – one of the most nutrient dense cruciferous vegetables you can keep in your refrigerator – these dark leafy greens are off the charts in Vitamin K content, and super high in Vitamin A and C among many other nutrients
  • pomegranate – Loaded with anti-oxidants + Vitamin C + Vitamin E + fiber
  • walnuts – high in those hard to find omega-3 fats, minerals, and anti-inflammatory properties

Let’s quickly step by step our way through this little dish so you can get to making it and enjoying all the bright flavors + show stopping health benefits.

selecting the squash

 

There’s many possible options here. I am particularly fond of the delicata variety because of it’s creamy sweet, almost brown sugar flavor, and relative quick cooking time since the flesh is not very thick, but if you can’t find/don’t have/don’t like delicata squash some easy substitutes would be:

  • acorn or carnival squash
  • little sugar pumpkins, tops cut off and hollowed out

The main thing to keep in mind is to choose a squash that has an edible skin. Any of the varieties that I mentioned above fit that criteria 👌🏽

In order to get the most flavor out of the delicata squash, you will roast it first separately.

This is gonna give you a beautiful and deep caramelized SWOON WORTHY flavor that carries through the whole dish.

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

While the squash is roasting, the kale, mushrooms and bacon are transformed stove top in a single skillet, one step at a time. The timing should be just about perfect. Squash roasted + stuffing complete all at once. So dang satisfying when that happens!

selecting the mushrooms

 
You really can take selecting the mushrooms in any direction that your little heart desires. I have made it with a mix of sliced crimini’s in combination with this little chef’s sampler pack that had oyster mushrooms, and several small mushroom varieties. I’ve also made it with a crimini + shiitake + portobello combination. All were equally delicious and satisfying.

No matter what type of mushroom you choose, the one important thing to do is to make sure they’re all cut into mostly equal sized pieces, so they all cook in about the same amount of time.

Roasted delicata squash stuffed with kale and maple cinnamon roasted mushrooms is literally bursting with brilliant seasonal flavor and color!  Roasted delicata squash stuffed with kale and maple cinnamon roasted mushrooms is literally bursting with brilliant seasonal flavor and color!
 
They are pan roasted with a little maple syrup and cinnamon with some of the drippings left from cooking the bacon (if you’re using bacon, otherwise you will start fresh with a few tablespoons of your cooking oil of choice).

The mushrooms are then set aside on a plate, and the kale is then gently sauteed with some broth and garlic in the same skillet, until bright green and tender.

Everything is then folded together to marry all the flavors, piled high into the squash, and heated again gently in the still warm oven before topping with the bright pomegranate and toasty walnuts.

If you’re eating this as a meal on it’s own, plan for about one half per person if the squash are large, or two halves if they are small.

If you’re serving it as a side dish, I recommend carefully cutting it into smaller pieces that are easy to pass and share!

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

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

equipment used for this recipe

Calphalon Nonstick Bakeware, Baking Sheet, 2-Piece Set

Cuisinart MCP22-30HCN MultiClad Pro Skillet with Cover

 
Print

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

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

  • Author:
  • Prep Time: 15 minutes
  • Cook Time: 45 minutes
  • Total Time: 1 hour
  • Yield: about 6 servings

Ingredients

  • 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 

Instructions

  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. 

Notes

  • 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. 

Did you make this recipe? I would love to know how it turned out for you! when you rate my recipes and leave feedback it helps me continue to improve. you can leave me a comment below, or snap a picture and post it to instagram with the tag @nyssaskitchen or hashtag #nyssaskitchen! xo

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