Orange and Cinnamon Roasted Delicata Squash

Sometimes the simplest things are truly the best, and that is undoubtedly the case with this squash. A very small number of ingredients come together to create a dish that is cozy, warming, nostalgic, and complex. This Orange and Cinnamon Roasted Delicata Squash has rapidly become a fall and winter go-to for us and I hope it will for you as well.

If you've followed this blog for a while, you're aware of my love for delicata squash. They're the easiest and fastest winter squash to work with because you can eat the skin. Just scoop out the seeds, cut them into slices, roast for about 20 minutes, and that's it- squash in no time. I also love their delicate, sweet flavor and creamy texture.

At the risk of stating the obvious, we eat a tremendous number of these little squashes during the winter. I can't get enough of them, and they're a great weeknight squash. We usually just roast them and toss them onto salads, although I also love stuffing them (check out my Holiday Wild Rice Stuffed Delicata Squash!). If you haven't explored delicata yet, now is the time.


My goal with this dish was to turn my everyday squash into something very festive and holiday-appropriate. This dish takes about 25 minutes from beginning to end, most of which is hands-off, which means you can easily add it as a side dish to holiday meals or winter get-togethers. Yet the flavors here are truly special and celebratory.

The flavors in this squash remind me of wassail, the holiday drink (google it if you're unfamiliar, you need to experience it!). Wassail is usually a combination of apple cider, orange juice, and warming spices, cooked all day so that the flavors meld. I've mimicked those flavors here by tossing the squash in apple cider, maple syrup, orange zest, cinnamon, and the tiniest bit of cayenne for warmth. It's a flavor combination that screams holiday.

While this is an incredibly quick and easy recipe, there's one little trick. I like to roast the squash plain until the slices are barely tender, then toss them in the marinade, then return them to the oven for another ten minutes. It's a (quick) extra step, but it prevents the maple syrup and orange zest from burning. Please trust me on this, it only takes about two extra minutes!

One other important point. You'll see that the ingredient list calls for a pinch of cayenne. This isn't to make the squash spicy! Rather, it's there to provide a tiny bit of warmth and depth, and to act as a counterpoint to the sweetness. Don't omit it, but don't go overboard either. It's the unidentifiable subtlety of the cayenne that really brings this dish to life.

Make this squash all winter long, whenever you need some comfort food. It will make your house smell amazing! You can serve it as a side dish alongside a festive meal, put it on top of salads, or use it as an element in a cozy Buddha Bowl. We've been enjoying it as a Friday date night nibble alongside this Holiday Spiced Rum Punch!

However you use it, this squash is like a cozy hug.

Please share your creation so I can see how you've interpreted the concept! Tag "The Rogue Brussel Sprout" on Facebook or hashtag #theroguebrusselsprout on Instagram.

The combination of maple syrup and the tiniest bit of cayenne is one I truly love and find so interesting. It makes an appearance in these Maple Rosemary Cayenne Roasted Nuts too.

Thoughts About Ingredients
(These are all just suggestions, since rogue is more fun than recipe)
  • 3 medium delicata squashes
  • Oil of choice for roasting
  • Generous salt and pepper
  • 2 tbsp apple cider (or orange juice, if you don't have cider)
  • 2 tbsp maple syrup 
  • Zest of a large navel orange
  • 1 tsp cinnamon
  • Pinch of cayenne. Note that the goal here isn't to make these "spicy"! The cayenne is just to provide some very subtle warmth as a complement to the cinnamon, so use some restraint. You don't need much.
  • Few sprigs of fresh thyme
  • Small handful of roasted or maple-roasted pecans
  • Optional greens and pomegranate arils for garnish
Thoughts About Method
(These are all just suggestions, be creative and make it yours)
  1. Preheat the oven to 425.
  2. Trim the ends off the delicata squashes, cut each in half length-wise, and scoop out the seeds. Then cut them into quarter-inch thick slices, making sure to get even slices so they cook at the same rate.
  3. Lay the slices out on a well-oiled baking sheet (or two, if needed) so that each has full contact with the metal. Salt and pepper generously, then roast for about ten minutes until barely tender.
  4. Meanwhile, in a large mixing bowl, combine the apple cider, maple syrup, orange zest, cinnamon, and cayenne.
  5. When the delicata slices are slightly tender, dump them into the mixing bowl and give them a gently toss so that each is fully coated in the marinade. Try not to damage the slices as you do this.
  6. Return them to the baking sheet and roast for another 5-10 minutes until fragrant, tender, and slightly caramelized.
  7. Place the roasted squash on a serving bowl. Top with the leaves of a few sprigs of thyme and a handful of roasted pecans.
  8. If desired, garnish with some greens and pomegranate arils. Serve immediately.


  1. Once the pomegranate is cleaned, this comes together quickly. It’s a very pretty side dish with a lovely combination of warm, fall spices.

    1. The Rogue Brussel SproutJanuary 2, 2021 at 12:43 AM

      Haha, yes, cleaning the pomegranate is always the unpleasant part. So happy to hear you like the cozy, warm flavors in this dish!


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