Ingredients

• 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

Instructions

1. 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.
2. 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.
3. Transfer vegetables to a platter, then drizzle some agrodolce over. Serve remaining agrodolce alongside.