• Make-Ahead

Ingredients

1. 1 buttercup or kabocha squash (about 2 pounds)—peeled, seeded and cut into 1-inch wedges
2. 1 butternut squash (about 2 pounds), peeled and cut into 1-inch cubes
3. 1/4 cup extra-virgin olive oil
4. 1/4 cup light brown sugar
5. Salt and freshly ground pepper
6. 1 acorn squash (about 1 1/2 pounds) —halved, seeded and cut into 1-inch wedges (with skin)
7. 1 delicata squash (about 1 pound), cut into 1-inch rings (with skin)
8. 2 tablespoons pure maple syrup
9. 1 cup heavy cream
10. 20 sage leaves, coarsely chopped
11. 2 tablespoons unsalted butter
12. Baby watercress and shaved pecorino cheese, for garnish

Directions

1. Preheat the oven to 350°. In a large bowl, toss the buttercup and butternut squash with 2 tablespoons of the olive oil and 2 tablespoons of the brown sugar. Season with salt and pepper. Spread the squash out on a large rimmed nonstick baking sheet. Add the acorn and delicata squash to the large bowl. Toss with the remaining 2 tablespoons each of olive oil and brown sugar and season with salt and pepper. Spread the squash out on another large rimmed baking sheet. Roast the squash for about 1 hour, turning once, until tender and lightly caramelized in spots. Arrange the squash on a large platter and drizzle with the maple syrup.
2. Meanwhile, in a small saucepan, bring the cream to a simmer with the sage and cook over moderate heat for 5 minutes. Remove from the heat and let stand for 5 minutes, then add the butter and season lightly with salt and pepper. Strain the cream into a heatproof cup. Drizzle it over the roasted squash, garnish with the baby watercress and pecorino and serve.

Make Ahead

The roasted squash and sage cream can be refrigerated separately overnight. Reheat in a 350° oven, loosely covered with foil.