- 2 delicata squash or butternut squash (about 4 pounds total), halved crosswise, seeded, sliced into 1/2"-thick rings
- 3 pounds sweet potatoes (about 7 small or 5 medium), cut into 3/4"-thick rounds
- 2 tablespoons extra-virgin olive oil
- 1 teaspoon crushed red pepper flakes
- 2 - 1/2 teaspoons kosher salt, divided
- 15 small sprigs thyme, divided
- 8 ounces fresh or frozen cranberries
- 2 cups red wine vinegar
- 1 - 1/2 cups sugar
- Preheat oven to 400°F. Toss squash, sweet potatoes, and oil in a very large bowl. Add red pepper flakes and 2 tsp. salt and toss to combine.
- Arrange on a rimmed baking sheet with 12 thyme sprigs. Roast, tossing once halfway through, until squash is golden brown and fork-tender, about 30 minutes.
- Meanwhile, cook cranberries, vinegar, sugar, and remaining 3 thyme sprigs and 1/2 tsp. salt in a medium saucepan over medium heat, stirring occasionally, until cranberries are soft and sauce is thick and syrupy, about 25 minutes.
- Transfer vegetables to a platter, then drizzle some of the cranberry agrodolce. Serve remaining agrodolce alongside.