You can start a day or two beforehand on the dishes that will complete your holiday menu: Slice squash up to a day ahead; refrigerate in a resealable plastic bag. Once cooked, squash can sit at room temperature, covered, for up to two hours.
- Vegetable oil, for baking sheets
- 3 acorn squashes (about 1 1/2 pounds each), halved, seeded, and sliced into 1-inch-thick crescents
- Coarse salt and ground pepper
- 1/2 cup packed dark-brown sugar
Preheat oven to 400 degrees. Line two rimmed baking sheets with aluminum foil, and brush with oil.
Lay squash pieces on baking sheets. Season with salt and pepper; sprinkle squashes evenly with half the sugar. Roast until sugar has melted, about 5 minutes.
Remove baking sheets from oven. Using tongs, turn over pieces. Season with salt and pepper; sprinkle evenly with remaining sugar. Roast until tender, about 20 minutes.