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Preheat oven to 425 degrees F. Line rimmed sheet pan with parchment paper and set aside.
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Wash delicata squash and slice in half lengthwise. Scrape out seeds and discard along with any fibrous flesh.
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Place cut side down on cutting board and slice squash into ½-inch slices to make half moons.
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Place squash into small bowl, add 1 Tbsp. avocado oil and ½ tsp. salt and toss to combine.
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Arrange squash on prepared sheet pan. Bake 15 minutes, flip slices over and continue baking additional 15 minutes until golden brown. Remove from oven and set aside.
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While squash roasts, in medium-sized saucepan, add oil and shallots, sauté 2-3 minutes until softened. Add couscous, toss with oil and sauté 2 minutes to toast lightly.
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Add vegetable broth, cinnamon stick and nutmeg. Bring to boil, turn heat to simmer, cover and cook 12 minutes.
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Remove lid from saucepan and add rosemary, cherries, ¼ cup of almonds and kale or arugula; toss to combine. Cover saucepan and cook 3-5 minutes until greens are wilted. Taste and adjust seasonings as needed.
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Serve warm on a platter topped with delicata squash slices, remaining chopped nuts and a few rosemary sprigs.