Preheat the oven to 400°F. Line a baking sheet with parchment for easy cleanup.
Slice the ends off of the delicata squash, then slice each squash in half lengthwise. Using a spoon, remove the seeds from each squash half, then slice the squash into 1⁄2-inch thick half moons. Transfer the squash to the prepared baking sheet.
Make the dressing! In a medium bowl, whisk the olive oil, vinegar, maple syrup, chipotle pepper, adobo sauce, garlic powder and 1⁄4 teaspoon of kosher salt.
Drizzle half of the dressing over the squash. Season the squash with the remaining 1⁄2 teaspoon of kosher salt and toss to combine. Arrange the squash in an even layer, making sure none of the pieces overlap. (If necessary, you can divide the squash between two baking sheets.)
Roast the squash on the middle oven rack for 15-20 minutes until tender and browned on the undersides. (Lift one piece up to check.) Transfer the pan to the broiler for 2-4 minutes (broilers are fickle!) until lightly browned on top.
Transfer the squash to a serving plate and drizzle with half of the remaining dressing. Top with goat cheese, scallions, cilantro, and pomegranate arils and drizzle with the remaining dressing. Serve immediately.