Step 1: To make dressing whisk together first 2 ingredients in a cup or bowl and then gradually whisk in the oil; season with salt and pepper.
Step 2: To make the salad: preheat oven to 400 degrees F. Brush 2 rimmed baking sheets with oil and then spray then with the cooking spray. In a small bowl whisk together vinegar and sugar and set aside.
Step 3: Cut squash halves crosswise into 1/4 inch thick slices and then arrange them on the baking sheets; brush with oil and sprinkle with kosher salt and pepper. Roast 5 minutes; brush with sugar-vinegar mixture; turn squash over and brush with mixture and roast for another 5 minutes. Roast for another 15 minutes or until squash is tender when pieced with knife. Cool on the baking sheets ****This can be done 4 hours ahead of time and let stand at room temperature.
Step 4: On 10 plates arrange 5-6 endive leaves and then place the squash slices in the center of each plate. Scatter the apples, cheese and cranberries over the squash. Drizzle dressing over all.
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