Preheat the oven to 400 degrees.
Place the butternut squash on a sheet pan. Add 2 tablespoons of the olive oil, 1 tablespoon of the maple syrup, 2 teaspoons salt, and 1 teaspoon pepper. Toss together, spread out in a single layer, and roast for 30 minutes, tossing twice, until tender and starting to brown.
Meanwhile, in a large saucepan, combine the rice, 3¼ cups water, and 1½ teaspoons salt. Bring to a boil, stir, lower the heat, cover, and simmer for 25 minutes. Turn off the heat and allow the rice to sit with the lid on for 10 minutes. (This will differ from the directions on the package.) If there is liquid left in the pot, drain the rice.
For the vinaigrette, in a glass measuring cup, whisk together the remaining 1 tablespoon of maple syrup, the orange juice, balsamic vinegar, white wine vinegar, mustard, 2 teaspoons salt, and 1 teaspoon pepper. Slowly whisk in ½ cup olive oil and set aside.
Pour the warm rice into a large serving bowl. Add most of the vinaigrette and combine. Add the squash, scallions, dried cranberries, and almonds and toss well. (As the dish sits, it may need the extra vinaigrette.) Taste for seasonings and serve warm or at room temperature.
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