Preheat the oven to 425°F and line two sheet pans with foil.
Wash the outside of the squash. Cut it in half lengthwise and scrape out all of the seeds. Cut off the top and bottom of the squash and then cut the remainder into ¼- to ½-inch pieces.
On one of the sheet pans, toss the squash with 2 tablespoons of olive oil and season with salt and pepper. Arrange the slices on both sheet pans so that they have plenty of space. Roast for 20 minutes. Remove the pan from the oven, flip the squash and roast for 15 minutes more, or until golden.
While the delicata squash is roasting, combine the vinaigrette ingredients in a small jar or bowl. Shake or whisk to combine.
When the squash is roasted, transfer it to a large bowl and add about ⅔ of the vinaigrette. Toss the squash well until it evenly coated with the sauce.
Transfer the squash to a serving bow and serve hot or at room temperature. Serve the extra vinaigrette alongside the dish.
Nutrition facts are sometimes provided below and are calculated using an online calculator. With specific brands of ingredients and additions, omissions, or substitutions the nutrition facts may change. We encourage you to use your own nutrition facts calculator to obtain the most accurate nutrition facts for your meal.