- 1 buttercup or kabocha squash (about 2 pounds)—peeled, seeded and cut into 1-inch wedges
- 1 butternut squash (about 2 pounds), peeled and cut into 1-inch cubes
- 1/4 cup extra-virgin olive oil
- 1/4 cup light brown sugar
- Salt and freshly ground pepper
- 1 acorn squash (about 1 1/2 pounds)—halved, seeded and cut into 1-inch wedges (with skin)
- 1 delicata squash (about 1 pound), cut into 1-inch rings (with skin)
- 2 tablespoons pure maple syrup
- 1 cup heavy cream
- 20 sage leaves, coarsely chopped
- 2 tablespoons unsalted butter
- Baby watercress and shaved pecorino cheese, for garnish
- 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.
- 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.
The roasted squash and sage cream can be refrigerated separately overnight. Reheat in a 350° oven, loosely covered with foil.