How to Make It
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.