Roasted Fennel & Delicata Squash with Olive & Parmesan Breadcrumbs

1. Position racks in upper and lower thirds of oven; preheat to 275°F.

2. Arrange bread in an even layer on a rimmed baking sheet. Bake on the upper rack until completely dry, but not browned, 15 to 20 minutes. Let cool. Place in a sealable plastic bag and crush with a rolling pin or mallet into pieces the size of a pencil eraser. Set aside. Increase oven temperature to 400°.

3. Meanwhile, trim squash, cut in half crosswise and scoop out the seeds. Slice into 1/2-inch-thick rings. Toss the squash in a large bowl with 1 tablespoon oil and 1/4 teaspoon each salt and pepper. Arrange in an even layer on a large rimmed baking sheet. Toss fennel in the bowl with 2 tablespoons oil and the remaining 1/4 teaspoon each salt and pepper. Arrange on another large rimmed baking sheet.

4. Roast the fennel on the upper rack until browned on the bottom, about 15 minutes. Flip the fennel and place the squash on the lower rack. Roast, flipping the squash once, until the vegetables are tender, about 20 minutes more.

5. Meanwhile, heat the remaining 3 tablespoons oil in a small skillet over medium heat. Add garlic and cook until golden brown, about 3 minutes. Remove with a slotted spoon or tongs to a cutting board. Add the reserved breadcrumbs to the pan and cook, stirring often, until golden and crispy, about 3 minutes. Remove from heat. Finely chop the garlic and stir into the breadcrumbs along with olives, Parmesan, parsley and thyme.

6. Transfer the roasted vegetables to a serving platter. Drizzle with vinegar and sprinkle with the breadcrumbs.

Tips

To make ahead: Prepare breadcrumbs (Steps 2 & 5) without Parmesan; store airtight at room temperature for up to 1 day. Add Parmesan just before serving.