- 2 pounds thin-skinned winter squash, such as acorn, buttercup or kabocha—washed well, halved lengthwise, seeded and sliced crosswise 3/4 inch thick
- 1/4 cup plus 2 tablespoons extra-virgin olive oil
- 1 tablespoon finely chopped flat-leaf parsley
- 1 teaspoon finely chopped marjoram
- 1/2 teaspoon finely chopped thyme
- Kosher salt
- Freshly ground black pepper
- 2 tablespoons maple sugar (See Note)
- 2 tablespoons red wine vinegar
- 1 small shallot, minced
- 10 ounces bitter salad greens, such as baby arugula, frisée and Belgian endive (about 16 cups)
- Shaved hard cheese, such as Toussaint or Parmigiano-Reggiano, for serving (See Note)
- Preheat the oven to 375°. On a rimmed baking sheet, toss the squash wedges with 2 tablespoons of the olive oil and the parsley, marjoram and thyme. Season with salt and pepper and spread the squash in a single layer. Roast for 20 to 25 minutes, turning once, until just softened. Sprinkle 1 tablespoon of the maple sugar over the squash and roast for 15 minutes longer, until the sugar just starts to caramelize. Flip the squash, sprinkle with the remaining 1 tablespoon of maple sugar and roast for 15 minutes longer, until the pieces are tender and golden. Let cool.
- In a large bowl, whisk the vinegar with the shallot and remaining 1/4 cup of olive oil. Add the greens, toss to coat and season with salt and pepper. Transfer the greens to plates or a platter and arrange the squash on top. Shave hard cheese over the salad and serve.