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Chili Maple Roasted Winter Squash | flavorthemoments.com

Chili Maple Roasted Winter Squash

Chili Maple Roasted Winter Squash is winter squash roasted to perfection with chili powder and maple syrup, and tossed in an maple orange vinaigrette.

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For the squash:

  • 8 cups winter squash cut into 1 1/2" cubes I used 2 cups each red kuri, kabocha, delicata, and butternut varieities*
  • 2 tablespoons extra virgin olive oil
  • 1 tablespoon maple syrup
  • 2 teaspoons chili powder
  • 1/4 teaspoon cayenne pepper

For the vinaigrette:

  • 2 tablespoons apple cider vinegar
  • 2 tablespoons fresh orange juice
  • 1 1/2 tablespoons maple syrup
  • 1 teaspoon dijon mustard
  • 3 tablespoons extra virgin olive oil
  • salt and pepper to taste


Prepare the squash:

  • Preheat the oven to 350 degrees. Toss the squash in the olive oil, maple syrup, chili powder, cayenne pepper, and salt and pepper, and spread in a single layer in a large rimmed baking sheet. Roast for 35-45 minutes or until the squash is very tender. Set aside to cool slightly.

Prepare the vinaigrette:

  • In a small bowl, whisk the vinegar, orange juice, maple syrup, and dijon mustard until combined. Add the olive in a steady stream while whisking constantly until the dressing has emulsified. Add salt and pepper to taste.
  • Place the squash in a large bowl. Add the enough of the vinaigrette to coat the squash and gently toss until combined. Serve warm and enjoy!


  • *You don't have to use all (4) varieties of squash here -- any variation will be great! Delicata, kabocha, and red kuri squash don't require peeling, and add a wonderful texture and color. I definitely recommend using at least one of them.
  • *See my tips on the best way to cut each squash in my post.
  • Recipe inspired by the cookbook A Good Food Day by Marco Canora.


Calories: 172kcal, Carbohydrates: 23g, Protein: 2g, Fat: 9g, Saturated Fat: 1g, Polyunsaturated Fat: 8g, Sodium: 76mg, Fiber: 6g, Sugar: 11g

Nutrition is estimated using a food database and is only intended to be used as a guideline for informational purposes.

Did you try this recipe?Be sure to tag @flavorthemoments with the hashtag #flavorthemoments on Instagram so I can see what you made!