Step 1

Adjust oven rack to center position and preheat oven to 400°F. Toss squash pieces with 2 tablespoons (30 ml) olive oil and season with salt and pepper. Arrange in a single layer on a foil-lined rimmed baking sheet. Bake until squash is tender throughout and well browned around the edges, 45 minutes to 1 hour. Remove from oven and allow to cool completely before attempting to remove from foil. Carefully remove squash from foil using a thin metal spatula and transfer to a large bowl. Set aside.

Step 2

Meanwhile, pick leaves off of kale stems into a large bowl and roughly tear with hands; discard stems. Drizzle with 1 tablespoon (15 ml) olive oil, season with salt and pepper, and massage until well-coated in oil. Transfer to a foil-lined rimmed baking sheet and bake until wilted and crisp in some spots, about 10 minutes. Remove from oven and transfer to bowl with squash.

Step 3

Combine cinnamon, paprika, nutmeg, cloves, cayenne pepper, and brown sugar in a large bowl. Add nuts and 1 tablespoon olive oil (15 ml), season with salt and pepper, and toss to coat. Transfer to a rimmed baking sheet and bake until toasted, about 5 minutes. Remove from oven, allow to cool slightly, then add to bowl with squash and kale.

Step 4

In a medium bowl, whisk together shallot, maple syrup, mustard, and vinegar. Whisking constantly, drizzle in remaining 1/4 cup (60 ml) olive oil. Season to taste with salt and pepper.

Step 5

Add cranberries to bowl with squash, kale, and nuts. Toss with half of dressing, taste, and add more dressing as desired. The dressed salad can be stored in the refrigerator for up to 5 days. Let it come to room temperature or briefly microwave until warm before serving.