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Preheat oven to 350°F. Place squash, shallot, and fennel on a baking sheet. Drizzle veggies with 1/8 cup of vinaigrette, season with cumin and cinnamon and place in the oven. Roast veggies for about 15 minutes or until tender and slightly golden brown. Remove from the oven and let cool to room temperature.
Divide kale and chard between plates, top with grapefruit segments and roasted veggies. Drizzle with remaining dressing right before serving.
Combine vinegars, honey, and dijon in a medium bowl whisk to combine. Slowly whisk in olive oil in a thin stream until blended. Season to taste with salt and pepper, refrigerate until ready to serve.
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