Photo by Katie Noble / Styled by Catrine Kelty

The easiest way to cook a winter squash—short of sticking it in the oven whole and waiting for it to soften and collapse—is to cut it in half and roast it with butter and brown sugar. As many ways as this has been done, there’s little that can improve the simplicity of lightly caramelized squash with a pinch of cinnamon and lots of sweet butter, but here I’ve tried serving it as a dessert instead of a side dish. Roasted with a pinch of ancho chili along with maple syrup and “pie spices,” I’ve topped it with a scoop of ice cream and a crumble of fried oats for crunch. It’s so easy and delicious you’ll make it even when you’re out of ice cream!

Serves 4

2 Acorn squash, Sweet Dumpling or Honeynut, halved and seeded
½ stick plus 2 tablespoons butter, softened
¼ cup dark brown sugar
¼ cup plus 1 tablespoon Grade B maple syrup
¼ teaspoon plus 1 pinch sea salt
¼ teaspoon plus 1 pinch cinnamon
¼ teaspoon plus 1 pinch nutmeg
¼ teaspoon plus 1 pinch allspice
¼ teaspoon ancho chili powder
⅓ cup quick-cook oats
Vanilla ice cream, for serving

Preheat oven to 400°F. On a parchment-lined rimmed baking sheet arrange the squash cut side up (use 2 trays if the squash is large). Using a spoon, blend together the ½ stick butter, brown sugar, ¼ cup maple syrup and ¼ teaspoons of the spices. Spread over the entire flesh of each squash and roast in the oven for 45 minutes.

After 45 minutes, spoon out the accumulated melted butter-sugar liquid into a small bowl and set aside to cool slightly. Continue to roast squash until deeply browned and caramelized and soft all the way through when pierced with a toothpick, another 10–15 minutes.

While the squash roasts, make the fried oats. In a nonstick skillet, melt 2 tablespoons unsalted butter and add the oats, 1 tablespoon maple syrup, pinch salt, pinch cinnamon, pinch nutmeg and pinch allspice. Stirring constantly, cook oats until browned but not dark. Remove from the heat and immediately pour onto a plate to cool—be careful as the oats can go from perfect to burnt in a matter of seconds!

Place a roasted squash half on each of 4 plates, scoop a big spoonful of vanilla ice cream into each cavity and drizzle with the reserved liquid. Sprinkle fried oats on top and serve.

 Notes:
• If you have any liquid left over, save it in a jar to use on your pancakes!
• You can use granola in place of the toasted oats, just remove any dried fruit and warm it in the oven before sprinkling.

This recipe appeared in the Fall 2018 issue as part of a larger story on Winter Squash and Pumpkins.