Roasted Sweet Potato and Delicata Squash with Cranberry Agrodolce
['4 delicata 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 cranberries', '2 cups red wine vinegar', '1 1/2 cups sugar']
Preheat oven to 425°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 1 hour.
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 35 minutes.
Transfer vegetables to a platter, then drizzle some agrodolce over. Serve remaining agrodolce alongside.
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