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In mixing bowl whisk together 2 tablespoons maple syrup, 1 teaspoon pie spice and cider vinegar. Slowly whisk in grapeseed oil and season with salt and pepper. (Can be made two days in advance, covered and refrigerated.)
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In small dish microwave ¼ cup maple syrup on high for 30 seconds; stir in cranberries, cover with plastic wrap; allow to sit for at least 30 minutes or overnight.
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Preheat oven to 475F. In large mixing bowl combine olive oil and remaining ½ teaspoon pie spice. Add butternut squash cubes; toss to coat. Line a heavy duty rimmed baking sheet with parchment paper. Arrange squash in single layer; season with salt and pepper. Roast 15 minutes; turn squash over; roast until tender (5-7 minutes longer). Cool to room temperature (can be made day ahead, covered and refrigerated. Bring to room temperature before assembling salad.).
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In large mixing bowl toss greens with three-fourths of vinaigrette. Divide onto 6 serving plates. Arrange squash, bacon, red onion and pepitas over greens.
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Drizzle with remaining vinaigrette.