Roasted winter squash with cranberry agrodolce is festive and full of Italian flavor. Make the sauce while the squash roasts on a sheet pan and everything is ready in about 30 minutes!
Wash the squash well and dry thoroughly with a kitchen towel. Do not peel it.
Cut the ends off the delicata squash, stand it on one end, then slice it in half lengthwise and use a spoon to scoop out the seeds. Place each half cut-side down, then slice into half circles that are about ½" thick.
To cut the acorn squash, lay it on its side and carefully cut off the stem end. Then place it cut-side down, cut in half and scoop the seeds out. Place each half cut-side down and slice it into half circles or slice lengthwise along the ridges.
Preheat the oven to 425°F. Place the racks in the upper and lower third of the oven. Separate each type of squash on two sheet pans, drizzle each with 1 tablespoon of olive oil, season each with ½ teaspoon of kosher salt, toss to coat.
Bake for 15 minutes, then remove the sheet pans and flip the squash pieces over. Return to the oven, placing the pan that had been on the top rack on the lower rack and vice versa. Bake for another 5-15 minutes until golden brown and soft, transfer to a serving plate.
While the squash roasts, make the cranberry agrodolce sauce. Mince the shallot and chop the sage finely, then use a microplane grater to grate the garlic (or mince it finely.)
Place a medium skillet over medium heat. Add the remaining 2 tablespoons of olive oil and once shimmering, add the shallots and a tiny pinch of kosher salt. Cook, stirring frequently until soft and translucent, 3-5 minutes. Add the garlic and sage and stir constantly for 30 seconds to 1 minute, until fragrant. Add the vinegar, honey, and cranberries and bring to a simmer, reduce heat to low and cook, stirring occasionally, until sauce is reduced by about ⅓ and is thick enough to coat the back of a spoon. It should still be pourable.
Pour the agrodolce sauce over the roasted squash on the platter, top with chopped hazelnuts and serve.
Notes
Roast your own hazelnuts if you have time: If you can find raw hazelnuts, roast them at 350°F for 8-10 minutes, then chop them. Freshly roasted nuts taste so much better, and if you're making this for a holiday or special occasion, it's worth the little bit of extra effort.
Watch the heat on the sauce: Keep the heat low and reduce slowly. The honey could scorch if the heat is to high, and you don't want to over-reduce it.
How to make it vegan: Substitute agave or maple syrup for the honey in a 1:1 ratio.
Make ahead: The agrodolce sauce can be made one day ahead and stored in an airtight container in the refrigerator. Reheat in a covered sauce pan on low until just warmed through. Don't reduce it any more.
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