Roasted Winter Squash

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Without the intent of overselling this simple, seasonal side dish, I will mention that my husband recently purchased an acorn squash so that I would make this recipe.

Initially, I thought this purchase seemed odd, as he is not particularly fond of orange vegetables.  He said that he remembered this recipe from last fall and suggested I mention here that he is quite a fan.

Well suited to a weeknight pork or beef dinner, this healthy and satisfying side is equally perfect alongside a Thanksgiving turkey.  For easy last-minute assembly, cut the squash earlier in the day and store in an airtight container or plastic bag in the fridge until ready to cook.

Roasted Winter Squash
Kabocha squash is similar to other winter squashes and has a delightfully creamy texture. Delicata and acorn squash are also delicious and, like kabocha, do not require peeling. The skin softens when cooked and is completely edible. Peeled butternut squash may also be used. If you have more than 2 ½ pounds, I recommend doubling the topping ingredients.

Yields 4-6 side dish servings.
  • 1 winter squash (2 – 2 1/2 pounds; kabocha, delicata, or acorn squash all work well; see notes)
  • 1 tablespoon pure maple syrup (may substitute honey)
  • 1 tablespoon brown sugar
  • 1/4 teaspoon each kosher salt and freshly ground pepper
  • 1 1/2 tablespoons coconut oil, melted (may substitute olive oil)
  1. Preheat the oven to 350 degrees F. Liberally grease a baking sheet and set aside.
  2. Cut the squash into wedges (about 1 – 1 1/2-inch thick) and place in a large bowl. (see notes)
  3. In a small bowl, mix all other ingredients. Pour the mixture over the squash, and toss to evenly coat. (I find this easiest to do with my hands. I also prefer to do this in a bowl instead of directly on the baking sheet. With a bowl, it is easier to get more of the topping on the squash and less residue on the baking sheet where it becomes harder to clean once baked.)
  4. Spread the squash pieces, cut sides down, in an even layer on the baking sheet and bake for 25-35 minutes or until just tender. Precise time will depend on oven and thickness of pieces. Use a sharp knife to test for doneness. Look for a golden brown color on the side touching the baking sheet and a hint of firmness remaining in the squash.
  • I adore the use of coconut oil in this recipe. It creates great flavor and aroma without tasting overtly of coconut. A hint of pure maple syrup is delightful as well, but honey and olive oil may be used in place of these ingredients.
  • A sharp chef’s knife makes cutting winter squash easier. However, if you struggle to do this, you may microwave or bake the whole squash just long enough to slightly soften. Pierce the skin with a knife first. In this case, simply adjust the later baking time down slightly.
The Fountain Avenue Kitchen

To achieve the golden brown, caramelization that tastes so good–and this applies to all veggies, not just squash–lay the cut vegetables on an oiled baking sheet with the flat side down. It is the side that is in contact with the hot metal sheet that will brown first. Roast, undisturbed, until the early side of the estimated cooking time. Then, using a metal spatula, peek at the undersides to see if they are browning. If the pieces are sufficiently browned but not completely cooked, flip them over. If the pieces are not quite cooked and could use more color, continue roasting without flipping. You will get to know how long this takes in your oven. I roast most vegetables until they are just tender without flipping. In many ovens, keeping the veggies in the oven until both sides are golden will result in a mushier vegetable than may be desired.

In case you are not familiar with it, this is what a kabocha squash looks like. (Buttercup squash are very similar but have a flatter top.) Along with acorn and delicata squash, these varieties are excellent options for this recipe as peeling is not necessary. The skin is edible–nutrient rich, too–and will soften as it cooks. Butternut squash is a delicious option, too; simply peel first.

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  1. Christie

    This was great! I need to work faster, my coconut oil was starting to harden before I got it in the oven! I even sprinkled a little bit of brown sugar over them after I flipped them.

    My kids liked them too!

    Can’t go wrong trying one of your recipes!

    1. Ann

      I just love how the flavor of the coconut oil and maple syrup complement the squash. So glad you enjoyed, too, Christie!

  2. Beverley Hart Press

    Thank you for sharing your recipe. I just made a similar dish to this but I love the sound of maple syrup. This is certainly going to be on my Christmas day lunch menu. Lots of love to you Xoxo