Yield: 4 servings
Heat the oven to 400°F (200°C). Line two large baking sheets with parchment paper. (If you have a large oven, you can roast everything at once; otherwise, it’s best to roast the squash first and then the grapes after.)
In a small bowl, combine the salt, chile powder, red pepper flakes, paprika, and black pepper.
In a large bowl, toss the butternut squash with 2 teaspoons of the olive oil and three-quarters of the spice mixture. Arrange in a single layer on the prepared baking sheets, leaving plenty of room in between the chunks. (No need to wash the bowl.) Roast for 20 minutes, then flip and continue to roast until the squash is tender and edges are lightly browned, 15 to 20 minutes more. Slide the parchment onto a wire rack to cool (you’ll be using one of the baking sheets again).
In the same bowl used for the squash, toss the grapes with the remaining ½ teaspoon of olive oil and the remaining spice mixture. Arrange the grapes in a single layer on a parchment-lined baking sheet and roast, shaking once or twice, just until the grapes start to burst, 8 to 10 minutes.
To make the vinaigrette, whisk together the garlic, vinegar, mustard, honey, paprika, and salt. Gradually whisk in the olive oil until emulsified. Fold in the grated Parmesan.
Toss the kale with half of the vinaigrette and arrange on a platter. Tuck the squash chunks and grapes among the kale leaves. Scatter the shaved Parmesan over the top and drizzle with the remaining vinaigrette. Serve warm or at room temperature.
Food52. (2017). Food52 mighty salads: 60 new ways to turn salad into dinner. Ten Speed Press.